Insomnia DxD
by HiddenHill
Summary: Nathan Weslock, a teenage genius with a lot of free time on his hands and an unhealthy obsession with solving puzzles is led to Kuoh to try and find a challenge worth his time. Join him as he battles with his insomnia, clashes wits with enemies, pops pills (which may or may not be prescribed), and gets on every female's nerves... or in their pants... usually both.
1. Chapter 1

**Insomnia DxD**

**This story is going to take place right after the Raynare arc when Asia becomes a part of Rias's Peerage. The only difference would be that Raynare managed to escape unharmed from her encounter with the Occult Research Club. Of course, the more favourites and follows this story gets the more it'll be worked on, reviews and PM's telling me what you guys liked or disliked about it are also always appreciated.**

**Disclaimer: I do not Own Highschool DxD**

**Chapter 1: Pilot**

* * *

**Kuoh Academy**

As he splashed his rest deprived face with cold water from the sink in one of Kuoh's male bathrooms, Nathan's thoughts filled with dread as he remembered that he would be expected to walk out of that bathroom door any second. Not because of the annoying ringing of the school bells signalling the end of his lunch break, or even the teachers and their countless boring lectures that awaited him. No, the very reason for this young man's reluctance to step outside of his temporary sanctuary was much more serious, much harder to ignore, and much more irritating.

As Nathan finished scrubbing his face in a vain effort to wash away his chronic fatigue he heard a polite yet authoritive knock on the door, he knew it was time. He turned the tap off and looked up to the mirror in front of him to see the reflection of a pale young man in his late teens with short length dark grey unkempt hair staring back at him with exhausted yet piercing blue eyes each coming with a distinct dark shadow under them which spoke for the amount of time their owner spent sleeping, which was quite literally none at all. It was convenient for him though, as his lack of care towards his appearance successfully managed to distract from his naturally handsome features, after all this young man's philosophy was the less attention the better.

With a sigh he reached into his blazer pocket and took out a half empty plastic yellow see-through bottle containing white oval shaped pills. After removing the white cap from the bottle he gently shook it until two pills rolled into his palm. As per his routine he quickly swallowed the pills and felt his migraine fade slightly.

Putting the pill bottle back into his school blazer pocket he walked normally to where he had left his support crutch, he reluctantly picked up his medical aid knowing that as soon as he walked out of that bathroom to greet his nemesis he would have to limp for the rest of the school day in order to keep up his façade as a cripple.

Why is this teen faking a disability I hear you ask? Well it's quite simple really, any action Nathan takes outside of the social norms that is noticed and called out by a classmate, a peer, a teacher, or any figure of authority could simply be stopped in its tracks by playing the "I'm a cripple, leave me alone card" and Nathan would exploit this fact to the utmost. After all, out of fear of social pressure not many people would actually stand up to question someone labelled as a pity case by the rest of society.

Except for her… Nathan's nemesis within the school and Student council President Souna Shitori, lesser known within the confines of the school as Sona Sitri, heiress to the Sitri clan of the 72 pillars of devil nobility, also the very person laying siege to the bathroom he was currently avoiding her in. Nathan grabbed his crutch at the handle and placed it's shoulder rest beneath his underarm, after limping five steps to check if it looked convincing enough he reached for the door handle and emerged from it to be greeted by the sight of Souna Shitori and Tsubaki Shinra, the student council president and vice president.

"Ah President Shitori and vice president Shinra, what a beautiful day to be stalking cripples into the one place they know you can't follow them in." Nathan sarcastically quipped as he laid eyes on the two women waiting for him outside of the bathroom. Both of them wore the same Kuoh academy female school uniform. Naturally Tsubaki being more endowed in the chest area filled the uniform better than Souna, not to say Souna wasn't visually pleasing in her own way.

Souna was a woman in her late teens that had black hair styled in a bob cut. She had porcelain skin and violet eyes behind a pair of black fully rimmed glasses with oval shaped lenses. Tsubaki, her second in command and queen of her peerage was a tall buxom woman with long straight black hair that fell just below her knees, she had split bangs and a heterochromatic pair of eyes, the left being violet like Souna's while the right was light brown. She too wore glasses but unlike her king's pair, her's were semi rimmed with a blue frame and rectangular shaped lenses.

"I'm sorry Mr. Weslock, but you have business with the student council. I'd like for you to see me in the student council room after school and before you ask, yes, your attendance is mandatory." The student council president ordered.

"Unless this is a booty call for a threesome I'm not interested" retorted the male. Surprisingly both Souna and Tsubaki kept a calm demeanour without showing any signs of disgust at the young man's perverted sarcasm. Truth be told this was not the first run-in they have had with the young boy so by this time they were getting use to his antics.

"Please refrain from saying such indecent things in public Mr. Weslock, as the head of the student council and the prime representative of Kuoh academy's student body I can't afford to have my reputation tarnished. I hope you understand and I'll see you in my office after the last bell rings" Sona retorted before making her exit along with her vice-president causing Nathan to roll his eyes at her.

As the two women of the student council made their exit Nathan began walking to his own class, his lessons usually felt like they dragged on and on but because of the meeting with the student council president that awaited him, the last ring of the school bell couldn't have come late enough.

As the students began to pack their belongings into their bags Nathan stood from his seat making sure to be supported by his crutch. He didn't have any books to pack on the count of memorizing them all completely prior to his transfer to Kuoh academy. It only took him two days to memorise all the content in the text books he would need to pass the curriculum for this year so it wasn't much trouble, at least not compared to having to carry a bag full of thick hard cover textbooks while pretending to be disabled.

As he was preparing to make his exit he was intercepted by non other than the Student council president's most moronic lapdog, Genshirou Saji. Saji was a young man with short blond hair and grey eyes. He wore his school uniform without a blazer and always rolled his sleeves up, Nathan's educated guess was that he was going for the intimidating 'bad boy' look while also following the general dress code of the academy in fear of being reprimanded by Souna.

"Nathan Weslock, I've been sent to escort you to the student council, please follow me." And here you could clearly see exactly why Nathan though of Saji as no more than a lapdog, his master throws him a stick AKA Nathan and then sends her pawn to go fetch. Don't get it wrong though, Nathan didn't really have anything against Saji, in fact he couldn't care less about the blond pawn. It was just the fact that Saji followed Souna's orders without a hint of objectivity that irritated Nathan slightly, but that didn't really get into Nathan's skin so why should anyone else give a damn?

Saji stepped aside to let Nathan pass through the door and the two began walking to the student council room, although it took longer than usual since Saji had to slow down to match Nathan's speed, little did the blond know that Nathan was only limping so slowly to drag out the time before his encounter with the student council president for as long as possible.

Eventually the two of them were standing before the door leading to the student council which Saji politely knocked on. After Saji heard the president call out from her desk for them to enter the blond opened the door and allowed Nathan to step inside the room first before doing so himself.

"I brought him President" Saji announced as he stepped to the side to join his fellow student council members minus Sona and Tsubaki who were situated on the desk across the room, Souna being sat in the chair and Tsubaki standing by her side.

"Thank you Saji".

As Nathan limped closer to the desk he noticed how everyone was situated, it was rather peculiar that the entire student council aside from the president and vice president would just stand to the side instead of doing their student council duties, if all of their work was done then that would mean that they could all go home. The question was why they didn't, and it was also a question that Nathan knew the answer to, but he decided keep his mouth shut for now and play it off, at least for a little while.

"You've really outdone yourself this time president Shitori, I ask for a threesome and you prepare an entire orgy! How thoughtful" Nathan remarked as he looked around at all of the beautiful women that formed the student council… and then there was just Saji giving him an irritated look. Nathan expected the girls to be at least a little disgusted by his comment but to his surprise they all seemed to either ignore what he said or be unbothered by it. Souna must have instructed them to pay him no mind prior to his arrival, smart move.

"Do you know why you're here Weslock?" Souna asked, completely dismissing Nathan's entering joke.

"I know it probably isn't worth my time. But please… go on."

"Well you'd be wrong. I've called you regarding a number of different misconducts, the most important one being your incomplete university progression form". Souna announced as she brought out a sheet of paper from inside a folder lying on her desk and pushed it across the table for Nathan to look at. "You're supposed to apply to at least three universities one year in advance and yet you haven't even listed one. Also, as a third year in Kuoh academy, you are obligated to join and remain a member of at least one after school club in order to have something to put on your university application" Souna reprimanded while fixing her glasses in place.

Nathan took a minute to think about his options, he knew Souna wouldn't leave him alone until he permanently joined a club but he didn't know of any clubs that he'd fit in. Joining a random club wasn't an option as he'd probably get kicked out in no time flat for mouthing off. Starting his own club was also out of the question because for that Nathan would need the approval of the student council president and he doubted Souna would approve of any kind of club that Nathan would be interested in starting… although to the student council president's defence a strip tease club in the school would require a lot of money to run. Finally Nathan came up with a solution, or so he though.

"I've seen a group of guys going around peeping into the female changing rooms and taking photos a bunch of times, can I join that club?" Nathan asked, but seeing both of the president's brows arch he already had an idea of her answer.

"That's not a club Mr. Weslock" Souna stated, feeling a little ire for a certain friend's brown haired pawn and his two perverted friends for tarnishing the academy's reputation to a relatively new student.

"Then what is it?"

"A loophole in Japan's sexual crime prosecution system…"

"…"

"Now if you don't mind I'd like to move on to the complaints issued against you from your teachers." Souna announced and looked up from her list of formal complaints by the faculty to gauge Nathan's reaction. The grey haired teen just sighed in exasperation but otherwise stayed silent. Souna saw this as a sign for her to continue and so she looked down at the sheet of paper before her and began reading the report out loud.

"Aside from frequently showing up late to classes, in a lesson in religious studies you weren't paying attention during a lecture on Shintoism. The teacher complains that as he was explaining how all of Japan's small islands were said to be the children of the primordial gods Izanami and Izanagi, he caught you staring into space and decided to call on you to answer the next question" Souna paused to make sure Nathan was paying attention to her. Satisfied in seeing that his focus hadn't drifted off to something else she continued.

"The teacher called on you and asked you why the Goddess Izanami wanted to bring destruction onto earth and you replied- and I quote ''{She was probably just salty about Hiroshima and Nagasaki.}'' I understand this was intended as humour but please keep in mind that others could get offended by comments like these". Souna looked back at the boy standing before her. She turned her gaze towards the other student council members and to her disappointment she saw some of the girls trying not to giggle at the reply she quoted, she gave them a stern look and after they got the message she continued… all the while Nathan sported his own smirk.

The student council president sighed and continued "It has also been my personal observation that you constantly have those shadows under your eyes, please make sure that you're getting enough sleep at least on school nights". After hearing this Nathan just gave Souna an eye roll.

"Great plan! I'll just politely remind my insomnia that this is my final year of Highschool and ask it to go easy on me. Why didn't I think of that?" Nathan retorted sarcastically, Souna could tell by his tone that he was getting irritated. Evidently this wasn't a topic that she should pry on. Seeing that all of her points were made she decided to conclude this meeting.

"That would be all for now Weslock, please make sure to improve your behaviour in the near future. I would also like you to write a letter of apology to your religious studies teacher for not paying attention during their lesson and also for making rude comments. Before said letter is delivered you are to run it through me for approval, am I clear Mr Weslock?" Souna asked knowing that Nathan most likely didn't intend to comply with her request, but that didn't matter. The slap on the wrist was nothing more than a forefront concealing the real reason that she had the grey haired teen brought to her, the actual reason was yet to come.

"Crystal. May I be excused now president Shitori?" Nathan requested in a deadpan tone, he was a little irritated with how demanding Souna's words sounded but it's not like he really cared about the way he was talked to.

"Very well, Saji please see him out" Souna requested and looked at her male pawn, he nodded in understanding of the underlying message of her words. Saji approached Nathan and escorted him to the exit, making sure to open the door for the latter. As Nathan stepped outside of the room Saji ever so gently brushed his arm on the collar of Nathan's blazer.

This was it. This was the actual reason why Nathan had been called into the student council room in the first place. To understand why that subtle contact was of such high importance we must go back a few days during the aftermath of the Occult research club's initial encounter with the fallen angels.

Rias had managed to eliminate three of the four fallen angels that had attempted to steal her newest servant's sacred gear. The only one left was Raynare, the ringleader who had managed to escape elimination at the hands of the red haired heiress. Despite Rias insisting that her peerage could handle tracking the fallen angel down alone, Souna didn't relent and as a result she had sent her own peerage out to patrol Kuoh town for any signs of the rogue fallen angel. Just as they were planning on giving up on the search, Saji in his best efforts had actually managed to spot her. Instead of direct confrontation, the blond had wisely decided to follow her instead.

This led to Saji finding out what Raynare was actually doing, she herself had been tailing someone and on closer inspection this turned out to be none other than Nathan Weslock, the boy who had transferred to their school a little over a month ago. The student council had no idea why Raynare would go after a seemingly normal teenager, but looking at who her previous targets were this matter was definitely worth looking into.

And now here the student council was in the present day distracting said teenager with academic discipline just for the opportunity to place an audio transmitting tracking and communication device on his clothing to monitor Nathan without him noticing. Nathan had to admit to himself that this was a well thought out cover that would've convinced him had he not been the hyper observative person he was.

As Nathan was heading home on his usual route he noticed that it wasn't crowded like it was every other day. In fact, that would be a harsh understatement, the area was practically a ghost town today. It could've been because the citizens of Kuoh just didn't appreciate the great weather they had today and so decided to stay inside their homes as a result…or it could just be the fact that Nathan had just walked into a magic barrier that disconnected him from the outside world.

Limping ahead while supporting himself with his crutch, Nathan noticed the first person he saw since leaving Kuoh academy. As he got closer the person revealed herself to be an attractive young woman with silky black hair that went down to her hips, she had violet eyes and a well-endowed slender figure and wore what appeared to be a school uniform consisting of a dark red jacket with a golden coloured letter "P" embroidered on her chest as a top layer. Underneath this she wore a white undershirt with a red bow and a green skirt.

As Nathan approached to walk by her she stepped in front of him, blocking his path.

"Are you Nathan Weslock?" the girl asked with a sweet voice which made Nathan halt his footsteps and look at her with curiosity.

"That depends, who's asking?" Nathan replied as he leaned into his crutch to balance himself better.

"My name is Yuuma Amano… I've watched you on your way to and from school and I think you're really cool… would you please become my boyfriend?" the now named Yuuma shyly stumbled out her request and enthusiastically bowed at Nathan. Nathan took his time to look the woman up and down, paying particular attention to the way she was dressed and how she carried herself.

"Damn…did it hurt when you fell from heaven" Yuuma giggled at the recycled pick up line that the grey haired teen had just used on her, not really because of the humour in it but more because of the irony of it in relation to what she actually was. Yuuma decided to play it off and continue with her goal of seducing Nathan.

"You're going to make my blush" The fallen angel put on a fake expression of embarrassment in an attempt to sell her act. Unfortunately for Yuuma, Nathan wasn't buying it.

"No I'm serious… you're a fallen angel" Yuuma tensed inside as she heard the teen's statement, her smile strained slightly as she tried to maintain a calm demeanour. All she could think to do was to play dumb in the ridiculously futile hope that Nathan would doubt his words enough to convince himself that he had confused her with something or someone else.

"W-what are you talking about…I don't understand" Yuuma couldn't believe her cover was blown so easily. She had been taking the utmost hair in completely eliminating her fallen angel aura, it should have been next to impossible for even a supernatural being with trained sensory prowess to detect her, yet this human had done it in a matter of seconds.

Realising that the girl before him wasn't going to give up on her act until he proved how he found out what she was, Nathan gave a bored sigh in preparation to list out the evidence which led the teen to his deduction.

"There's no school in all of Kuoh town that's name begins with the letter "P" which you've stupidly decided to embroider on your jacket. Since you already knew my name I can assume that you were indeed watching me go to and from school regularly as you said. But since Kuoh academy is also situated relatively far from any other school it would mean that you wouldn't have enough time to follow me _and_ attend your own classes. This tells me that you're lying about being a student. To add insult to injury, like the idiot you are you've decided to wear a winter uniform during the summer semester which makes me certain that you're not even Japanese. No regular human would have the resources or the interest to go into a foreign town under the guise of a Highschool student just to ask some cripple out on a date". Nathan paused his explanation and noticed that the woman in front of him was faltering more and more with every word he spoke. He watched as the irrefutable evidence he delivered chipped away at the resilience of Yuuma's farce piece by piece. Nathan sensed that it was just a matter of time before the alleged fallen angel gave in to reveal her true self.

Inside of the student council room, Souna and her peerage were listening in on Nathan's encounter with Yuuma through the transmitter. Everyone was in awe at what they heard from the device which broadcasted Nathan's conversation. Every devil in the room simply marvelled at the fact that Nathan had managed to deduce that Yuuma wasn't human just by looking at her uniform. Rias, who had been invited by Souna to listen in on the encounter along with her respective peerage was the first to speak.

"His skills in deduction are rather remarkab-" Is all the red haired heiress got to say before Souna angrily shushed her into silence. Rias was irritated by her friend's attitude but before the buxom redhead could say it, Nathan's voice was once again heard.

"Now that we've established that you aren't human, I can also safely say that you're also not an angel since they wouldn't intrude into another faction's territory unless provoked and given that you are so obviously hiding from the devils that occupy this town you clearly aren't one of them, which leaves the naughty crow's club. So could you cut the act now?" Nathan finally concluded. Having had enough of the grey haired teen's insults, Yuuma finally decided to drop her poorly maintained charade.

"FINE!" Yuuma's clothes suddenly disappeared in a bright flash of light to be replaced by an outfit that Nathan could only describe as something out of the dark side of the playboy mansion. Yuuma was now wearing a black bikini made out of a material which resembled leather and a black shoulder guard with three spikes on her right shoulder. The now confirmed fallen angel also sprouted a pair of black angel wings with which she immediately took flight and hovered into the air above Nathan "And for the record, the name's Raynare! Remember me as the one who slayed you!"

"Can I just remember you as the chick that started stripping on the sidewalk?"

"…"

"Let me take a wild guess why you're here. You were likely sent to Kuoh town to take out something that your boss deemed a threat to your faction, most likely a powerful sacred gear wielder. I'm guessing that since this is devil territory you were also sent out with a team to back you up in case the devils became hostile. Since you don't have your group with you here I can assume that you failed in your original assignment and your team was killed as a result. You decided that instead of going back to your boss empty handed, you should take back some sort of consolation prize to save your skin and so you desperately scoured this town for anything that might possibly satisfy your boss, and this brought you to yours truly."

Raynare's mouth lay agape, a trait which was shared with everyone at the student council room who was listening in on Nathan's follow up deduction.

"He guessed it almost exact-"Souna managed to comment until she was exaggeratedly shushed by an over enthusiastic Rias with what Souna believed to be a petty revenge for the way Souna interrupted the Gremory heiress a few moments back.

Back at the place of the confrontation, Raynare manifested a purple light spear in her right hand and pointed it down at the ground at Nathan's general direction. "Staring at your smug grin makes my want to throw up, but you're right. Once I found out that a member of the famed Weslock family resided in Kuoh I knew it was my only shot to return unpunished."

The student council room fell dead silent, every devil in the room apart from the newly reincarnated Issei and Asia were suddenly trying to piece together where they had heard that name before. It didn't take long for them to recollect the stories and rumours that they had heard about the infamous Weslock family, a group said to be so ridiculously rich yet isolated that even some supernatural beings deemed them to be nothing more than a mere rumour.

The realization that one of them had been hiding right under their noses this whole time hit the devils like a tonne of bricks. This was only reinforced by the fact that Nathan hadn't even bothered with an alias of any kind, he made no effort to disguise his name at all. All the devils had assumed that someone so rich would carry themselves more akin to an aristocrat rather than an irritable high school student. Another thing that worked in Nathan's favour was his image as a cripple, someone with the wealth and resources of the Weslock family would be able pay for the treatment of such injury, whether it'd be human made medicine, or a supernatural spell.

The student council had ultimately dismissed Nathan's surname as a mere coincidence when he first transferred weeks ago on the account of the aforementioned reasons. The silence in the student council room was broken when Nathan's voice was heard through the transmission receiver.

"I hate to rain on your scantily clad parade but the devils you've been avoiding like an athlete does piss tests are actually listening in on this conversation." Nathan casually remarked as he reached his hand around his back to fish for the device he knew Saji planted on him back in the student council room. After a few seconds of digging in under his blazer's collar he managed to grasp it and pull it out. Twirling the glowing pink orb around his fingers, Nathan realized that what he was inspecting was a magical communication device often used by devils to communicate with each other during rating games. "This device has allowed them to eavesdrop."

"You're bluffing!" Raynare's grip on her light spear faltered slightly as doubt entered her mind, if what Nathan was saying was true then that would mean that the devils who killed her squad could just sense the location of the transmitter and teleport to it, leaving her outnumbered. If that was the case, she was done for.

While this was happening, the student council was once again in awe at the realization that Nathan was aware of their spying since the beginning.

""He knew all along?"" Sona and Tsubaki exclaimed simultaneously.

Nathan decided that it was finally time to address the devils who were spying on him directly. The teen brought the orb shaped transmitter to his face so he could speak into its little microphone.

"I know you're there Souna, if you don't get your perfectly pear shaped ass over here this second I'll rat you out to your superiors for failing to protect Kuoh from intruders." Nathan once again leaned smugly into his crutch as he followed up with the rest of his threat. "I wonder who they'll replace you with…hopefully someone with bigger-" Before Nathan could get the final word out, a white glowing magic circle formed on the ground in front of him and out of it emerged Souna with Tsubaki by her side.

Upon seeing the Sitri heiress and her queen emerge from the magic circle, Raynare's blood ran cold. There was little to nothing she could do at that point. Souna decided to spare no time in dealing with the matter at hand and so she addressed the fallen angel.

"Raynare I take it? You have trespassed on territory occupied by the Gremory and Sitri clans of the seventy-two pillars. This is your last warning, leave this town now or face your demise at my hands, I won't ask again" Souna commanded with a reserved tone of authority. The Sitri heiress left no room for argument and it wasn't long before the startled fallen angel had made up her mind. With the option of the possibility of harsh corporal punishment weighted against her immediate death it came as no surprise that Raynare had decided to retreat to live another day. The fallen angel dematerialized her light spear and in mere moments she had teleported herself away from their presence.

"Took you long enough." Souna and Tsubaki turned to stare at Nathan with slight irritation evident by their expressions. By nature they were both reserved and prone to barely show any emotion at all, but Nathan's smugness was something of a near tipping point for them. Despite this, they appeared to keep their composure intact.

"I'd like us to talk in my office again, please come with us." With intention, the tone Souna used made that request sound more like an order, it either didn't bug Nathan or he didn't show it. The grey haired teen limped over to where the two women were standing without saying a word until he was standing beside them on the magic circle they had used to teleport to him. In his usual fashion he turned to the Sitri heiress next to him.

"I hope you're not taking me to get my memory erased because I know how that works. I've seen all of the Men in Black movies…even the porno parodies. 10/10 would recommend by the way, they did a great job on the female casting." Both women scowled inwardly as they motioned for the magical circle underneath them to activate, it soon began to spin and in a flash of light the trio had vanished.

Back at the student council office where the two peerages were awaiting the trio's return having heard the entire conversation through the receiver on Souna's desk. Soon enough Souna's magic circle appeared in the middle of the room and out of it emerged the Sitri heiress along with Tsubaki and Nathan.

Upon arriving, Souna and Tsubaki immediately walked to the desk where the former sat down with the latter taking her position by her side. Nathan stood in the middle of the room where the magic circle that brought them there had just vanished. Noticing that he was the centre of attention of the two groups the teen raised an eyebrow upon seeing Rias's peerage in the room. Did not being a moron really make Nathan stand out so much, or was there just something on his face? Nathan wondered as he took a second glance around the room. Noticing the long silence in the room, Rias decided to speak up.

"I don't believe we've met before, I'm Rias Gremory, it's a pleasure." Rias was a beautiful woman with white skin and blue eyes, her most prominent feature apart from her amazing rack was her long Crimson hair that reached all the way down to her thighs. Like Souna, Rias was wearing the Kuoh academy girl's school uniform. "And these are my beloved servants" Rias said as she gestured to the group beside her who all immediately bowed politely at Nathan.

"My name is Nathan Weslock" the young man introduced himself in response "and this is my beloved crutch…She's a little shy now but in private she calls me 'daddy'…" Of course Nathan delivered the last line with his usual sarcastic tone. It came as no surprise to Souna and the others who knew him that he wouldn't even bother to take an introduction with Lucifer's sister seriously. After Nathan gave his name, each member of Rias's peerage then took it upon themselves to give their individual introductions.

"Akeno Himejima, third year, pleased to make your acquaintance" Akeno said with a polite smile. She was a beautiful young woman with porcelain skin, violet eyes and silky black hair tied in a ponytail reaching down to her legs. She also had an incredibly buxom figure, even more so than that of her master and like all the women present in the room, she also wore the Kuoh academy female school uniform.

"I'm Asia Argento, second year, good to meet you!" Asia stumbled out. She was a young pretty girl with serene green eyes and golden blond hair that reached down to her back.

"Koneko Toujo, First year" Nathan heard a flat monotone voice introduce itself , due to its owner's short stature it was usually harder to notice that she was even there until she spoke, but Nathan noticed her straight away. The girl was of short height with a slim petite figure, she had hazel eyes and white hair reaching just down to her shoulders with split bangs framing her face and a black, cat shaped hairclip attached to her left bang. Nathan and the tiny girl briefly made eye contact but Koneko quickly looked away.

"Yuuto Kiba, Second year, let's get along"

"Issei Hyoudou, Second Year"

Issei and Kiba were the two males in the group aaaaaaaand that's pretty much all that Nathan remembered about them. After all he had much more important priorities, like not-so-discretely admiring that Akeno girl's rack. Nathan's appreciation of Akeno's body was cut short by the sound of the student council president clearing her throat.

"Now that we've been through introductions, I'd like to ask you some questions if you don't mind. And also, you should know that trying to leave is pointless, we've set multiple barriers around the premises." Souna stated. She doubted that Nathan would try to escape but assurance was her game, and precautions were necessary.

"Damn…Because that definitely put a stop to my plans of limping away to freedom…" Nathan retorted in a mock disappointed tone and tapped his crutch on the floor a couple of times for emphasis. Souna however, wasn't in a joking mood.

"We know you're faking that limp, so you can stop acting now. Also, haven't you been taught that feigning disabilities and conditions is extremely offensive to those who actually suffer from them?" Souna chided.

"Yeah… because that doesn't sound hypocritical at all coming from a perfect sighted devil wearing glasses" Nathan quipped, adding to Souna's already broad list of reasons to lose her patience. "And at least I didn't lie about my identity, Miss _Sona Sitri_." Nathan finished by heavily emphasizing the Sitri heiress's real name. He didn't even understand the need for Sona to use an alias, especially such an obvious one. Even if an alias was helpful in any way whatsoever to hide her position in this town, Rias's name would still be a dead giveaway.

"Firstly, I'd like to know how you found out that Kuoh was occupied by devils in the first place." Sona got straight to the point with her first question. Aaaaaaaand with that, the interrogation officially began. Nathan, sensing that this was going take a while instinctively reached for his blazer pocket and pulled out the same bottle of pills that he had back in the bathroom earlier today.

He popped the cap off the bottle and shook it until two pills landed on his palm. Nathan Looked at the pills in his hands and then turned to the devils, then back to looking at the pills and then back to the two peerages again. "Oh what the hell…" Nathan mumbled to himself as he shook the pill bottle again until two more pills rolled out to join the other two that were already sitting on his palm. Nathan quickly swallowed all four pills without a second thought and screwed the lid onto the bottle before putting it back into his blazer pocket.

"Might I ask what those were?" Sona enquired.

"If I told you they were laxatives would you let me leave?" Sona just rolled her eyes as the teen in front of her made his latest sarcastic remark...at least she hoped it was sarcasm. Wanting to move on from this matter, Sona once again asked her original question.

"Back to the topic, how did you know this was devil territory?" Sona pressed again.

"Simple, there's a church in this city that no one ever goes to, I figured that it must have been abandoned for a reason, most likely due to another faction moving in. Fallen angels who occupy deserted churches make it a point to destroy all of the religious objects there to spite God. However, that church had been left untouched meaning that this town was being occupied by species that can't go near it. Vampires don't live outside of Europe so that just narrows it down to you guys."

Hearing that explanation, Sona couldn't help but admire Nathan's raw deductive skill, sensing the various auras of supernatural beings was one thing but deducing what those beings had to be using logic alone was something else entirely. It would appear that she had gravely underestimated the grey haired teen.

Satisfied with Nathan's answer Rias decided to voice her own query. "But how did you know we were the devils running this town?" Before Nathan even had the chance to answer, Sona had already beaten hit to it.

"I believe I can answer that." Sona stated and turned to Nathan with a knowing smirk. "We're not talking to you in Japanese are we?" Sona asked to the confusion of most of the devils in the room who waited for an explanation to the Sitri heiress's question. "Devils and other supernatural beings have the passive ability to transcend language barriers, the humans that we talk to hear us in the language they are most familiar with." Realising what Sona was talking about, Nathan decided to finish the explanation himself.

"In class, everyone hears you guys talking in Japanese since this is the language that's spoken here, so when I hear you guys talking in the language I know best it's a dead giveaway". Nathan finished Sona's explanation and returned her smirk with his own.

This time it was Tsubaki who was curious about something, after a nod of approval from her king she turned to Nathan with her question in mind.

"To my knowledge, the Weslock family is one of the richest in existence with numerous ties to the supernatural world. I'm just curious as to what brings one of you here." At the mention of his family, Nathan's mood visibly fell. The entire room went quiet for a minute but Nathan quickly ended the silence.

"My family doesn't really have anything to do with me coming here, I don't even really talk with them very often. The reason why I came here was because of the high supernatural influence. It seems that wherever the supernatural goes puzzles and mysteries follow…and I like puzzles." Nathan's voice seemed a little off to Sona and Tsubaki, it was as if the teen was actively trying to force his voice to sound casual. As soon as his smirk fell from hearing Tsubaki mention his family they could tell that it was a topic the teen would prefer not to discuss, for one reason or another. Having experience with troubling family members, namely her overbearing sister, Sona understood Nathan and mentally noted to only bring that topic up if necessary.

With that, the student council president decided to get back onto the topic. "Well, I'm sorry to disappoint you but nothing that interesting ever happens here." Hearing Sona's reply, Nathan raised an eyebrow at the Sitri heiress. Sona already saw the sarcasm coming from Nathan before the teen even began to speak.

"Oh right… and I'm sure that Puma I'm-A-Hoe girl or whatever her name was who tried to kill me a few minutes ago was really out here just to sightsee with her friends…" For the first time in this meeting, Nathan actually had a legitimate question for the devils.

"What do you guys even do around here? I know devils sign contracts with humans, but what kind of things to you do for them?" Nathan asked, and to the credit of whoever decided to answer, that did sound like an innocent question, but little did they know that Nathan had ulterior motives behind it. Rias decided to answer this one.

"We do exactly what our flyers say, we grand any desire our client has for an appropriate fee, our policy is always honest billing and customer satisfaction." Rias said with a proud smile, meanwhile after hearing this Nathan rubbed his chin in thought.

"Damn…And here I've been spending hundreds of thousands of Yen messing around with human hookers…guess it's time for an upgra-"

"We don't offer services like that Mr. Weslock" Sona cut him off right then and there.

"But she specifically said _any_ desire! This seems like false advertising…I can sue for that you know?" Nathan Joked in a mockingly sarcastic tone of despair eliciting giggles from some of the girls in the room.

Having gained all of the information she needed for the time being Sona decided that it was time to dismiss Nathan from her office. "That would be all for now Nathan, thank you for answering our questions, you may leave now." Nathan just shrugged and turned around to walk out of the door when Sona's voice stopped him yet again. " And by the way I still expect you to hand in that letter of apology and join a club…and also you're no longer permitted to walk around the school with crutches." Without even turning around, Nathan could sense the smirk plastered on Sona's face as she said that.

"Fine then" adopting a smirk of his own, the grey haired teen walked towards the door and opened it. With one last look of acknowledgement to the two peerages, Nathan shut the door behind him as he left the room, leaving his no longer needed crutch behind to lean against the wall next to the door before heading out.

Soon after Nathan had left, both peerages decided to head out to work on their contracts leaving only the two kings and their respective queens in the student council room. Sona had been smiling to herself ever since she saw Nathan leave her office, something that Rias picked up on since it was peculiar, Sona rarely ever smiled and the redhead was even more surprised that her friend and rival would smile today of all days, when they had to deal with the one person in the school who caused the most trouble for the student council president.

"You don't smile like that very often Sona, what brought this on?" Rias asked. Sona wasn't really paying attention to what went on around her. She had been thinking about how exciting and interesting the rest of the school year would be now that someone with Nathan's intellect had arrived to challenge her, it appeared as if Sona had finally found her intellectual match.

"Huh? Oh…it's nothing" Sona answered with a slight hue of pink on her cheeks from being caught staring into space.

"Rias?" The two kings and their queens turned to the direction the voice came from to realise that it was Koneko, who'd stayed behind too without them realising.

"Yes Koneko, What is it?"

"It's about that guy…I've met him before, but back then he looked different…" Rias could sense some seriousness from within Koneko's monotone voice.

"Really… where did you meet him?"

**To Be Continued…**

* * *

**From the second chapter onward I'll be confirming one girl at a time who I've chosen for Nathan's harem at the end of every new chapter until the list is complete. But, whoever manages to guess the Television character that Nathan is based on will get the full list immediately…Let the games begin.**

**HINT: It's not Sherlock Holmes.**


	2. Chapter 2

**Insomnia DxD**

**Quick author's note-**

**Before you guys dig into me about how the first part of this chapter is unrealistic due to it featuring a pre-teen who professionally practices medicine, please remember that there was a time where a nine year old calculus prodigy would regularly hold lectures at Harvard for advanced mathematics. Also, I hate writing flashback scenes because I suck at them so I'll only have a few throughout the entire story.**

**Disclaimer: I do not own Highschool DxD**

**Chapter 2: Stray Cats**

* * *

In a crowded hospital waiting room filled with patients and their family members or friends a speaker sounded off notifying the awaiting crowd that it was time for the next patient to come into the only exam room located on that entire floor. Naturally the door to the room stuck out like a sore thumb being the only door on that floor apart from the door leading to the staircase that the patients used to get there. The waiting room itself looked rather dull apart from a decorative fish tank with three clownfish that resided in it situated at the waiting room corner closest to the exam room.

The door to the exam room opened and out of it came a middle aged woman with an extremely irritated expression on her face. The woman said nothing as she made her way through the crowded waiting room until she got to the door leading to the staircase.

"Stupid brat…" the woman muttered angrily before closing the door behind her.

Soon enough out of the same door that the woman had come from emerged a young boy. He looked to be no older than twelve and was of average height for his age. The boy had tired icy blue eyes with dark shadows under them and short dirty blond hair, he wore a tailored lab coat over a black t-shirt and jeans. On his chest there was a name badge that read "Dr. Nathaniel Weslock" that also came with a portrait ID photo. The preteen boy slowly walked to the middle of the room and looked around. The boy exhaled in exasperation at the sight of the crowded waiting room full of patients who all looked at him with confused expressions due to his attire in relation to his age.

"If you googled your symptoms on the internet after sneezing twice and read that you have terminal cancer, AIDS, Polio, or some other ridiculously rare fatal disease, please raise your arm…" The young man addressed the crowd, and like he predicted almost every person in the waiting room immediately put their hand up. Feeling a headache coming, the boy pinched the bridge of his nose and momentarily closed his eyes. "Of course you all did… Okay… what you all have is something much more serious…you all have a neurological disorder called Paranoius Idioticus. Fortunately, this particular disease can be cured by something called education, if you go back to school and redo 8th grade biology you should be fine…have a good day."

And with that, the preteen doctor turned and started walking back to his exam room. He turned back to see that all the people who were waiting for him in the waiting room had already started to file out one by one apart from two girls sitting next to each other in the corner of the room. One of the girls looked to be around ten years of age while the other one looked to be around Nathan's age.

The younger of the two was a cute looking girl that had shoulder length white hair with bangs that framed her face on which she wore a black, cat shaped hair clip and she also had hazel eyes and pure white skin. The older one was a beautiful young girl with black hair and eyes the same colour as her sister's. She looked to be just a little shorter than Nathaniel or 'Nathan/Nate' as he liked to be called.

Upon seeing the two girls Nathan frowned a little knowing that he would have to deal with another set of annoying patients who would probably also ask him how he became a doctor at such a young age just like the hundreds of patients before them had. Deciding with a sigh that it would probably be best to just to get this over with, Nathan called for the girls to follow him to the exam room.

The exam room itself was ordinary enough. It consisted of a single bed at the far corner of the room, a small desk which was situated in front of a window concealed by rows of blinds, three chairs in the middle of the room, and a sizeable cabinet on the side of the room opposite to the bed. With the two girls each sitting comfortably on a stool and Nathan leaning on the wall in front of them, the older of the two girls decided to speak up.

"Aren't you too young to be a doctor?" Ah, there it was… it was a little late since he'd usually get asked that before the conversation even reached the exam room, but it came nonetheless.

"Aren't you too young to be a legal guardian?" Nathan shot back with a casual shrug. In the girl's defence, Nathan was probably the only preteen doctor that anyone would ever see, but there was a reason for it. Albeit young, the boy was a genius and a prodigy able to become one of the best in anything he put his mind to. Medicine might seem like a peculiar choice at first glance but what the girls and any other patient that walked into his exam room didn't know is that Nathan didn't really have much choice of how to go about a career at this current stage.

Due to a particular incident he'd been part of in the past, Nathan had been left with two choices…either train in medicine to work at one of the few dozen free clinics that his successful older brother had established…or go back to living with his parents. For reasons many didn't know, constantly dealing with annoyingly moronic patients that pestered him about his age all the time was definitely the lesser of two evils for Nathan, but that wasn't the subject now.

"So what brings two young nekoshou to a clinic in the human world?" Nathan asked nonchalantly while staring at the ground. After a few seconds of silence on both girl's part Nathan looked up to see the two sisters staring back at him in disbelief. After rolling his eyes at the two girls before him, Nathan began to fill in the blanks for them as to how he found out what they were.

"Back in the waiting room, your little sister's pupils dilated from staring at the fish tank. Raw fish is enjoyed by Sushi enthusiasts… _live _raw fish on the other hand are enjoyed by cats or cat-like creatures. The fact that you're here alone without your parents also means that you're either orphans, or you've just run away from something that is hunting you… Judging by how well-groomed you both are I doubt that you're orphans and since nekoshou are the only species of nekomata that are currently being hunted I can assume that the reason you came here alone _isn't_ because mommy and daddy are at work…"

With Nathan's conclusion the older girl scowled inwardly knowing that she and her little sister had been found out. What was more frustrating was that she was using up a good portion of her energy trying to hide their auras so that they could get her sister examined without being undetected. The older nekoshou's biggest surprise was that instead of a supernatural hunter with trained sensory prowess or at the very least an adult doctor with decades of experience…they were instead found out by a mere preteen boy.

But thinking about all of those things was meaningless now… her main priority was to get herself and more importantly her dear sister to safety, which would have to start with them getting out of that clinic as soon as possible.

"Come on Shirone, we need to leave." The older nekomata said as she hurriedly began helping her tiny sibling off of her stool. As the two began to turn around to walk towards the door they once again heard the sound of Nathan's voice.

"I think you two would be better off staying put." Nathan casually suggested.

"Why? So you can turn us in to those bastards who're out for us?" The senior nekoshou questioned with outrage while making a point to cover Shirone's ears.

"No, so your little sister can stop bleeding out of her nose…"

At first, the black haired nekomata stood there in confusion until she turned to her sister to realise that Shirone had indeed started to bleed severely from her right nostril. To the older girl's horror, her little sister also appeared to get paler by the second as her blood rapidly dripped onto the floor.

"Kuroka, I feel..." The little girl began to collapse from blood loss as she called to her older sister. In a desperate panic Kuroka managed to catch the younger nekoshou just before she hit the ground.

"Shirone!"

"We need to lie her down." Nathan said as he helped Kuroka pick the barely conscious girl up to gently lie her down onto the medical bed in the corner of the room. Without missing a beat the boy formed a palm sized light grey magic circle which he placed over the younger girl's nose to stop the bleeding temporarily. He then conjured up two small bright green magic circles in each hand and moved them around Shirone's body as if they were scanning her body for something.

"You can use magic?" Kuroka inquired as she rushed to stand beside Nathan to see what he was using the magic circles for. After he finished examining Shirone's body and confirming that she was in stable condition, Nathan relaxed his hands and soon the magic circles dispersed. "So what's wrong with her?" Kuroka asked, overwriting her original question.

"I'm not sure yet, all I know is that it's in her blood…either way, right now you have bigger problems." Before Kuroka could ask the boy what he meant by his last remark, Nathan walked over to the blinds that prevented sunlight from shining into the room from its only window. He parted two of the blinds with his fingers to look through the window and after confirming his suspicions, he motioned for Kuroka to join him. Out of curiosity, the young nekoshou briefly left her little sister's bedside to see what Nathan was talking about.

As soon as Kuroka looked through the window her blood ran cold. A large magic barrier was rapidly forming around the general area of the clinic with both Nathan and Kuroka sensing that it was devil magic. The older nekoshou cursed under her breath for not noticing that she and her sister had been followed. The entire reason they were in a clinic at all was because Kuroka didn't want to take any risks regarding Shirone's health amidst they're escape. The black haired nekomata was aware that in doing so, she was running the risk of being found out even in a human clinic, but she didn't care. Shirone was all Kuroka had left and protecting her little sister was her number one priority ever since their parents died.

"Get your sister and hide under the bed…_now." _Nathan instructed with a serious tone leaving no option for disagreement. Without any other choice, Kuroka gave a small nod as she carefully picked her sister up and obliged. Once both nekomata were lying down under the bed, Nathan rushed to the cabinet on the opposite side of the room and took a towel which he used to wipe away the trail of blood leading to the bed that the younger nekomata had shed previously.

With all trails that could emanate any suspicion of the two nekoshou sisters being here taken care of, it was just the waiting game. Nathan, Kuroka and even the barely conscious Shirone all knew to expect a devil to show up where they were in moments. With the physical evidence taken care of all that was left was for Kuroka to conceal her and Shirone's auras until they were in the clear.

As predicted, a vertical yellow magic circle soon materialized in front of the door. From it emerged a tall, bald, muscle-bound man wearing dark leather armour all around his body with spiked guards on his shoulders, elbows, and knees. His most noticeable feature was a sizeable scar that cut through his left eye and eyebrow. Once the magic circle behind the man dispersed, there was an awkward silence in the room as the devil and Nathan were looking each other up and down. A few moments passed which felt like ages to the two nekoshou hiding for dear life under the bed until Nathan finally decided to break the silence.

"If you're looking for a steroid prescription you came to the wro-." Whatever Nathan was about to say was cut short on the count of the man unfurling two large bat-like wings which he then used to charge at the young boy until he had his hand around Nathan's throat, holding the blond boy against the wall by his neck. In response to this Kuroka protectively hugged her sister in a tight embrace to muffle the startled cry of the younger nekoshou.

"Shut up and listen you damn brat! Two stray devils came through here and since you're the only human in this entire building that didn't get removed from my barrier I know you can use magic and I know you know where they are!" The man commanded with a deep growl. After he finished talking he loosened his grip around Nathan's throat slightly to which the boy responded by desperately gasping and coughing for air.

"W-what did they look like?" Nathan asked in a weak voice. This was possibly the best answer anyone could've thought to say in that scenario. Had Nathan tried to lie or misdirect the devil right at the start, he would risk sounding too suspicious by being overly cooperative. Nathan knew that the best way to go about this sort of thing was to act like he was working for the man's best interest. Upon seeing that the boy would put up no resistance the man chuckled.

"Smart kid…" oh he had _no_ idea... "One of them was around your height and age, long black hair, yellow eyes. The other was a couple years younger, shorter white hair _with _a black, cat shaped hair clip and her eyes were the same as the first. The noble house of Naberius has set aside a small fortune for those who help in capturing those sneaky feline brats. But know this… if I find out that you've impeded this investigation even by a millisecond…nothing but a painful death awaits you…now where are they?"

Hearing this from under the bed, Kuroka couldn't help but let out a small tear trail down her face as she sobbed silently knowing that it was all over. It didn't take a genius to figure out that the young boy would obviously choose a generous sum of money over getting executed. It was an obvious no-brainer. One would think that having killed her high class devil master, Kuroka would be able to take out the one in the room without issue, but all the effort she put into escaping with her sister had strained her stamina to its limits. Even if she did manage to kill him, the house of Naberius would just send someone stronger on their tails. She could do nothing now but await their impending doom in silence.

Nathan on the other hand was more focused on the phrasing the devil used in his description of the two girls. For some reason he felt the need to mention the cat shaped hair clip that Shirone was wearing. The fact that the devil even bothered to mention that accessory meant that it was something of importance either to him or to the devil household who had called for the hunt for the two nekoshou. Nathan had to find out how valuable this cat shaped hair clip really was, and the only way he could do that was through comparison.

"Y-yes, I know where they are! They left through the exit at the _east_ wing of the clinic!" Nathan exclaimed as part of the lie he had put together. Hearing this, the man completely loosened his grip and let the boy drop down on his feet albeit staggering back against the wall due to the unexpected landing. The devil seemed to be satisfied by the boy's answer and turned to leave but Nathan wasn't done… now it was time for the test. "But before they left, a man intercepted them and took that girl's hair clip…I don't know why." As soon as Nathan finished telling his second lie, he found himself pinned in the same position again, this time with double the force.

"Which way did _HE _go? TELL ME!" the bald assailant practically screamed in Nathan's face, confirming the boy's suspicion that the hair clip _was_ indeed important.

"He left through the _west _wing exit, you just missed him!" Nathan lied and felt his airways clear as the bald man once again let go of the boy. Nathan's question now was no longer if Shirone's hair clip was important or not, now the only question remaining was _how _important it was. That question was soon answered by the bald man who had released Nathan from his grasp to take off into the sky through the only window in the room, sending shards of glass falling behind him, in the direction that Nathan had predicted…the _west_ wing exit.

That was it… Nathan now had his answer. The blond boy had intentionally structured his lie in the form of scales to weight the importance of hunting down the fugitive nekomata against that of attaining the cat shaped hair clip. Had the devil continued on his way to the _east _wing exit where he was told the nekoshou pair had left through, it would've meant that the sisters were the higher priority. However, the devil chose the _west _wing exit where he had been told the hair clip was instead. Nathan admitted he was very curious as to why the decorative accessory was of such high value, but right now he had some priorities of his own.

"The coast is clear, you can come out from there now" Nathan called out to the two girls. Kuroka opened her eyes for the first time since she embraced her little sister. It took a moment for her to register what had happened in the moments she believed would be her and her sister's last… they were saved! Kuroka slowly got up from under the bed and quickly pulled Shirone out with her. After a brief moment of rejoice shared with her sister brought on by the fact that they were still alive, Kuroka turned to Nathan.

"Why did you save us? They'll have you killed now." Kuroka asked in a tone of combined curiosity, gratitude, and a hint of concern for the boy. To Nathan the answer was simple, he wasn't too concerned about the consequences of harbouring the two girls, not even the prospect of being hunted and killed himself.

On the other hand…

"You guys are the first medical case I've had in months that can't be solved by an orangutan carrying a Band-Aid… I don't care if it's a man, an army, or even the four great Satans themselves, they're not laying a finger on you until I figure out what your sister has… oh, and also because of doctor-patient confidentiality and stu…"

Before Nathan could finish his sentence, he felt the new sensation of a pair of soft lips being pressed against his own. It only took a second for Nathan to realise that it was none other than Kuroka who had just initiated their first kiss. Deciding against pulling away, Nathan leaned in to further explore this new feeling brought on by their contact. After what to them seemed only a brief moment which was a bit over half a minute in reality, the two slowly parted without breaking eye contact.

"So that's it then? No dinner, no movie… just straight to first base?" Nathan asked with a coy smirk appearing on his face.

"Do you have a problem with that?" Kuroka retorted with a playful smirk of her own.

"Other than the fact that your sister has started to bleed again, no…" Nathan said in the same calm matter-of-factly manner he had used in his previous warning of Shirone's blood loss. On this occasion however, Nathan didn't let the problem escalate as he quickly walked over to the younger nekoshou to summon another small magic circle to stop the bleeding. "Lie down again." Nathan guided Shirone back to the bed and gently helped her climb up onto it to lie on her back. Nathan once again summoned his green magic circles to scan her body and dispersed them once he was sure the nekomata's condition was stable like before.

Nathan pulled up the two seats that the girls had sat on before and placed them next to the bed. He gestured for Kuroka to join him and they each sat in either stool to watch over the resting Shirone. A few minutes of silence passed and the white haired nekomata gave out a small adorable yawn and turned on her side facing the wall to fall asleep both due to the fatigue brought on by the whole endeavour that had just occurred and a little bit less so because of the blood loss. Seeing that her younger sister had fallen asleep, Kuroka turned to Nathan.

"You were wrong about us earlier…"

"Hm?"

"We are orphans…our parents died in a lab explosion a year ago. That's why we had to become devils…" Kuroka corrected in reference to Nathan's deduction prior to the arrival of the stray devil hunter.

"…" Nathan didn't know how to respond to that. Was he expected to apologise? Comfort her? Ahh women were confusing!

"It was fine at first…we were told we would be looked after and so I figured it was the best option for us…for Shirone…" Nathan didn't say anything. Instead he chose to position himself to face Kuroka, silently encouraging the black haired nekoshou to continue with her story. "But soon that bastard started using us for his sick and twisted experiments… he'd extract our sage energy, beat us when we wanted to stop and we weren't allowed food until he was satisfied…" Kuroka finished.

Nathan however was too occupied with focusing on the last thing Kuroka said to offer any kind of emotional response to the nekoshou's backstory. He kept replaying Kuroka's words in his mind.

'Beaten…starved…Shirone had no signs of physical trauma meaning her nosebleed wasn't caused by her master's beatings. Starvation on the other hand was much more likely, the magic scan showed that the problem was in her blood… Hypoglycemia? No, low blood sugar doesn't present that way in humans, youkai or devils for that matter. And even if it did, Shirone was a reincarnated devil, which means her evil piece would've protected her from things like this. Unless…' Nathan's eyes widened and a massive grin instantly found its way on his face as he quickly turned to Kuroka who was staring at the boy in confusion.

"I know what she has… Quick! Wake her up!" Nathan said as he bolted out of the room leaving Kuroka in an even more confused state. Nevertheless the senior nekoshou obliged to the pre-teen's request and gently stirred Shirone into consciousness. They soon saw the young man staggering back into the room with his hands full with what Kuroka correctly guessed to be packed lunches.

"Is that you're lunch?" Kuroka asked in confusion as to why Nathan was so excited about bringing food over, especially at a time like this.

"It's somebody's lunch" Nathan replied flatly as he placed all the bento boxes in front of Shirone and collected every sugar-based food type he could find in each box.

"Isn't that stealing?" Kuroka asked with a raised eyebrow directed at the pre-teen doctor.

"Yeah, you killed a high class devil and I jacked some guy's fruit pie…I'm such a monster." Kuroka rolled her eyes at the boy's sarcasm. But she was curious, what was the food for?

"Why are you giving her food?"

"Her blood sugar level is dangerously low, it's called hypoglycemia… the evil piece inside her is designed to sustain her body for as long as possible. But since she became a stray devil, her evil piece went haywire losing the ability to distinguish blood which lacked glucose from any other invading foreign liquid that wasn't supposed to be in her body, so the evil piece followed its instinct and pumped the blood it though was killing her out through the easiest possible exit…her nose." Nathan concluded. Kuroka was satisfied by the answer and felt great relief when she saw that as Shirone ate, her face started getting less and less pale until it was almost at its original healthy complexion.

"This didn't happen to you because you had your matured sage energy to sustain you in the absence of a functioning evil piece. As for your sister… as long as she rests and eats regularly, she'll be fine." Nathan finished talking and before he could do anything else, he found himself on the receiving end of a crushing bear hug of gratitude at the hands of the black haired nekomata.

* * *

"That was six years ago…the day before Sirzechs found me after she abandoned me…" Koneko had a sunken expression as she finished retelling her story. The tiny nekomata quickly found herself being hugged by Rias who did her best to comfort her servant while she was brought back to her painful memories.

"Do you think it was really him? Koneko said that the boy had _blond _hair?" Akeno chimed in. While there were some options in the supernatural world to permanently change one's hair colour, it wouldn't make any sense for Nathan to bother with cosmetic transformations given his dishevelled appearance on school grounds.

"It was him…he has the same scent" Koneko confirmed. As a nekomata, she had the ability to identify individuals by scent alone, even supernatural beings with considerable resources would find it hard to fool the enhanced senses of an experienced cat youkai.

"It definitely sounds like him… What do you think lady Sona?" Tsubaki turned to her king.

Sona clasped her hands together on her desk, thinking about Koneko's description of the boy the latter met years ago. From the nekoshou's description, Sona was sold on the idea that the man who had become her nemesis within the school and the young boy who saved Rias's rook and her older sister were one and the same. They both had the same piercing stare, those tired shadows underneath the eyes, that irritating and repulsive sarcasm, and of course…that spectacular talent of deduction and observation. It had to be him.

"As Rias' rook confirmed, I think it really was Natha-*ahem*… Weslock. Everything matches except for the hair colour. They even have the same name. It'd be foolish to overlook that, we already made that mistake once." Sona concluded, trying to cover up the slip of the tongue that almost made her call Nathan by his first name.

"One would think that you'd start calling him by his given name considering the way you were looking at him earlier lady Sona" Akeno teased.

"And what is that supposed to mean, Miss Himejima?" Sona asked in a stoic manner. But before Akeno could continue her teasing, she was quickly reprimanded by her master.

"Oh stop it Akeno. Sona wouldn't sink so low as to take interest in some pervert with an attitude." Sona raised a questioning eyebrow upon hearing Rias's words.

"Aren't you one to talk, Gremory? At least Weslock has a brain. You're pawn can only think about staring at breasts and causing trouble for the school."

"So you _are_ interested in him?" Rias asked, allowing a teasing smile of her own to make its way across her face in knowing that this was potentially another thing she could tease her friend about.

"I just admire his skill in deduction, that's all. And I don't think we need to worry about him too much. If he came to Kuoh with ill intent he would've done something by now." the Sitri heiress assured and once again turned to Rias. "Besides, I'm sure you have bigger problems to worry about instead of my affairs." Hearing this, the Gremory heiress' smile fell as she remembered the forced engagement that her family had arranged for her. In a few weeks Rias would be expected to marry Riser Phenex, the third heir in line for the position as the head of the house of Phenex, a noble pure-blooded devil household among the 72 pillars. The agreement had burdened Rias for years, but the Gremory heiress could do little to nothing as a means of escaping that fate.

"You're right. Thank you for your time Sona, we'll be leaving now." With that, Rias, Akeno, and Koneko all walked towards the door to the student council room and promptly made their exit.

* * *

As next week came around it was the same old deal for Nathan who was keeping his head down in class as usual waiting for the lessons to pass so that he could once again go to the student council room, give in that stupid and unnecessary apology letter so that her royal pain in the ass, Sona could approve it and allow the grey haired teen to go home and get on with the rest of his sleepless life.

Except, there was also another issue that Nathan had to take care of before he went home apart from his issues with the student council. The night prior, Nathan received an e-mail asking him to come to the old school house after he was done with Sona. The sender didn't include their name in the email and most likely used a throw-away account, meaning that whoever they were and whatever they wanted with Nathan, it had to be kept secret. Obviously the email had to be from someone who was in either the student council, or Rias's peerage given that the sender knew about the apology letter that Nathan had to hand in to Sona at the end of the school day. Nathan's best guess was that it was from Shirone, or Koneko as she went by nowadays, but the reason behind the email was beyond even Nathan's guess.

Back at the student council room last week when he and Koneko had made contact for the first time since he saw her last six years ago, Nathan immediately realised that she had recognised him as the boy who saved her and her sister from that stray devil hunter. But he didn't see the reason why she'd want to contact him now, Nathan doubted that she'd email him with a throwaway account just to ask him to catch up. But who knows? Koneko was only the prime suspect so it could've been anyone else from the people present at his last confrontation with Sona.

In the end, there was only one way to find out who the sender of the email was and that was through going there and seeing for himself. Thinking about it, that was probably why the sender remained anonymous. Making a play on Nathan's curiosity was a good strategy to lure him in since he most likely would've ignored the email had the sender revealed their identity, no matter how polite the invite, Nathan wasn't interested in bending to their will unless he had an agenda behind it, and that he did, and it was one that he'd been carrying with him for a while now.

Hearing the last bell signalling the end of the school day, Nathan packed up what little equipment he had on his desk and began walking on his way to the student council. Luckily for him, his prior reputation as a cripple combined with his dishevelled appearance allowed for him to quickly sink almost completely out of his peer's sight, which came in handy as nobody even bothered to ask him how he'd stopped needing the assistance of walking crutches over one weekend.

As he approached the door leading to the student council room, Nathan reached into his blazer pocket and routinely pulled his bottle of pills out. Opening the bottle, he gently shook it as usual and let two pills roll onto his palm. After swallowing the pills, Nathan pocketed his bottle and then knocked on the door.

"HONEY, I'M HOME!" Nathan yelled through the door already picturing the headache that Sona was about to receive from dealing with the teen's antics. With a sigh of irritation, the student council president called for Nathan to enter and so the young man opened the door and walked in. After opening the door to the room, Nathan noticed that this time he and Sona were alone in the student council room.

"I trust you have the letter?" In response to Sona's inquiry, Nathan unzipped his bag and took out a white envelope and handed it to the Sitri heiress. Once she had opened the envelope, she took the paper from inside and after unfolding it she began to read through it. Seeing this as a chance, Nathan began to slowly back away in an attempt to discretely excuse himself from the room.

"You aren't dismissed yet." Sona called out without even looking away from the letter. "I need to approve this before you go." Nathan gave a tired sigh and decided to take a seat in front of Sona as she read his letter.

"Dear Mr. Yuzuru, regarding the offensive comment I made during our last lesson, I would like to say that I am very, very, very, very…very, very, very, very…very, very…" Sona's eye twitched as she skimmed through the page and turned it around to find nothing but the same sentence from the beginning being continued by the constant repetition of the word 'very' one after the other until it reached the bottom of the second side. "This is just one sentence with the continuation of the word 'very' In between it." Sona complained with ire in her voice as she thrust the sheet of paper at Nathan.

"But I poured my heart and soul into it!" Nathan sarcastically exclaimed in defence, in response to this, the student council president rubbed her temples. Huh, what do you know? Nathan really did give her a headache…

"You even forgot to write 'sorry' at the end… the letter just ends with the word 'very'." Sona criticized again, earning herself an eye roll from Nathan.

"I'll just fill it in with a marker… besides, it's not like Mr. Yuzuru is expecting the letter anyway, if I write a genuine letter he probably wouldn't even read past the third line. He doesn't want an apology, he just wants the satisfaction of knowing that someone was kissing his ass, that's all he's looking for." Nathan casually assured Sona in a ridiculously vain effort to get her to approve of the letter. Instead, the Sitri heiress promptly tore the paper in half before scrunching both of the pieces into a ball and throwing it into a small waste basket by the side of her desk.

Realising that Nathan wasn't going to budge on that matter, Sona decided to change the subject. If this was any other student, Sona would've been more reprimanding and harsh, but Nathan was a special case. Throughout all of the run-ins the student council has had with the insomniac, they have never actually successfully corrected any part of his misbehaviour. Prohibiting Nathan from faking his bad leg didn't count as Nathan would've stopped that act anyway since his cover was blown and now the devils in the town knew who he was. Wasting time and energy arguing about a petty thing such as an apology letter was beyond Sona's scope of interest, so she decided to move along. Clearing her throat, the Sitri heiress once again addressed Nathan.

"I've noticed that you still haven't fixed your sleeping schedule" Sona was of course referring to the obvious shadows underneath Nathan's tired eyes. At this point, they were one of the distinct features that defined his appearance since they had been around ever since he transferred to Kuoh over a month ago, it also didn't help how much they stuck out to the people who saw past his cover as a cripple, namely the student council and the occult research club.

"Well, certain thoughts keep me up at night… global warming…imagining you naked… imagining myself naked...imagining us naked toge-"

"Okay, enough" Sona interjected, cutting the insomniac off in favour of continuing the topic. "The reason I brought this up is because I wanted to know if you've looked for medical attention regarding your sleeping problems. The Sitri territory has one of the best hospitals in the underworld, If you like, I can schedule an appointment for you to see if they can help your insomnia if it's that serious of an issue." Sona wasn't sure what to expect in Nathan's reaction to her offer. On one hand, she expected him to agree since there weren't any strings attached… at least a far as Nathan knew. On the other hand, Nathan did come from one of the wealthiest families in existence, so accessing the most elite medical experts on his own shouldn't be much trouble for him. The question was why hadn't he done that already? And so, the purpose behind Sona's offer was that at the very least, even if Nathan declined it, at least she could find out more about him to satisfy her growing curiosity about the teen.

Nathan knew the Sitri heiress's game though, and even though he found Sona charming, he wasn't in the mood to play. "I appreciate your concern, but I can wipe my own ass." Nathan replied flatly, Sona though he'd say something like that so she honestly wasn't surprised, but as a classmate she couldn't help but feel at least a little concerned. "Now would that be all, president Shitori?"

"Not quite, you still haven't joined a club…" Sona adjusted her glasses as she reminded Nathan that he had not yet signed up for an extra-curricular activity as required for all third year students of Kuoh academy. Nathan sighed in boredom at the prospect of having to join a club, it was clear that our grey haired insomniac protagonist wasn't keen on fitting in with other people. Sona suddenly gained a smirk of excitement as she thought of what she believed was the ideal solution.

"Weslock, do you play chess?" Nathan was a little confused at the random question but it was only for a few moments until he figured out what the Sitri heiress was getting at.

"You want me to beat you in chess for the right to not join a club?" Nathan deduced as his previous expression of mild irritation turned into that of intrigue.

"No, I'm proposing that you play me in chess for the right to become a pseudo member of the student council, you'll be one of us as far as the school is concerned but you won't be in my peerage. However, you'd still get to assist us in our devil duties if you wish, like hunting down stray devils and protecting Kuoh and such. It's the perfect arrangement… you said that you came to Kuoh due to the puzzles that were provided by the heavy supernatural influence. What better way to tackle and explore those puzzles than by going straight for the source?" As Sona proposed this, she couldn't help the small smirk she had as she knew that she had intrigued Nathan.

"This is the most ridiculous proposition I've ever heard… you're on!" Nathan agreed with a smirk as the two shook on the deal. Sona took out a small post-it notepad from a drawer on her desk and proceeded to write something down on it before handing the small sheet of paper to Nathan.

"We'll play at my house, this is my address, when would you be free to come?"

"Literally anytime… I won't be sleeping" Nathan deadpanned.

"Fine, then let's say… this Friday?" Sona suggested.

"Friday is fine by me, until then president Shitori." Nathan said as he stood up from his seat and turned to leave the room.

"Oh, and one more thing Weslock…" Sona called out, once Nathan turned to face the Sitri heiress, she continued "You can call me by my first name now, we're already well acquainted enough to move past formalities." Nathan chuckled a little.

"If you say so Sona, feel free to call me Nate. Nathan Weslock are my father, grandfather, great grandfather and so on" Sona's expression turned into that of slight surprise after hearing this.

"Really, so you're first name is also inherited?"

"No, I was lying… but imagine how cool it would've been if it was true" Nathan revealed, causing the Sitri heiress to let out a small laugh.

"See you tomorrow, Nathan."

"Later then, Sona." Nathan said as he walked towards the door, opened it, and walked out leaving the Sitri heiress alone in her office to look forward to their upcoming bet.

* * *

With that issue out of the way, it was now time for Nathan to make his way to the old schoolhouse where the occult research club was situated in. Upon entering the thought-to-be-abandoned building he noted how well maintained it looked compared to its view from the outside. Then again, that was the look that the peerage based in the building was going for, if the external parts of the structure looked abandoned and unused, the normal students wouldn't go near it, making it as good of a base of operations as any for supernatural activities.

As Nathan went up the starts, he saw the only door in the entire corridor. It had to be the door to the occult research club room. After walking up to it, Nathan leaned in to put his ear to the door.

Silence…

Okay, so maybe no one was talking. Nathan decided to make himself known by knocking on the door a couple times.

No answer…

"…"

Okay, so it sounds like there's no one there, but Nathan knew he was called to this exact location at this approximate time. Sona didn't mention any emergency to Nathan in their earlier discussion that would require the Gremory peerage to leave suddenly so there shouldn't be any reason for the room to be empty. Nathan didn't come all the way here just so that the person who sent him the email would be a no show. So in his usual nature, our favourite insomniac decided to explore. He started by twisting the handle of the door to allow himself in.

As he walked inside, Nathan observed the area to be a wood panelled room with Victorian styled furniture comprised of a small coffee table situated between two couches in the middle of the room. Looking to the left, Nathan could also see a desk where Nathan presumed that Rias sat in. In appearance it was similar to the one that Sona had back at the student council room. Looking on the right, Nathan could see an opaque set of curtains that stood out from the walls around it. Nathan approached it out of curiosity and pulled the fabric back to look inside.

In doing so, Nathan was greeted with what even the wildest perverts wouldn't ever dream of finding even in their horniest fantasies… the sight of Akeno Himejima, the occult research club vice president, nude as the day she was born and standing barely two feet away from Nathan, in what looked to be a shower room. She had one hand generously hugging her bountiful breasts while her other hand gracefully covered her nether region.

"My! I've been found." The nude beauty exclaimed in a sultry manner as a seductive smile formed on her face. Nathan looked the woman before him up and down, but to the thunder priestess' surprise it was not a look of perversion. His stare was more akin to being…analytical, and as he finished, his exhausted icy blue eyes looked directly into her violet pupils without even faltering for a moment. Akeno felt an odd sensation, she didn't know how to explain it to herself. It was as if Nathan was undressing her even beyond her nudity, it was like he was peering into her very being, boring into her very soul.

"What do you want from me, Himejima?" Nathan inquired, snapping the queen out of her trance-like state. She adopted a slight look of confusion in response to what the teen had just asked her. Seeing that he'd have to explain himself…as usual, Nathan sighed and fully stepped into the room as he let the curtains behind him fall back into place.

"You're body isn't wet and there's no steam in this room which means the shower wasn't turned on, so there's no reason for you not to have heard me knock before I entered the room given that the only things standing between us were a thin wooden door and a piece of fabric. You knew I was in the room and yet you didn't answer which means that you wanted me to come in here and see you like this. You're trying to seduce me. Smoking hot 10/10's… especially smoking hot _devil_ 10/10's like you wouldn't want to have sex with someone like me unless you had some sort of agenda. Which brings me back to my question…what do you want from me?"

* * *

"Okay, so your king is forcefully engaged to this high class devil guy from the Phenex clan called Riser, but she doesn't want to go through with it because she doesn't like him which somehow led to you appearing naked in front of me because…reasons? Did I sum it up right?" Nathan asked before swallowing two pills he had taken from his blazer pocket. He was sitting on one of the Victorian style couches in the occult research club with Akeno, now fully dressed in her Kuoh academy school uniform and sitting on the other couch across the coffee table.

"I was hoping that I could get you to help free Rias from her engagement…" Akeno had lost her sultry tone in favour of sounding more genuine, since Nathan had found out what her game was she decided that there was barely any point on trying to seduce the teen.

"You're a loyal friend Himejima, not many people would be willing to go that far for someone…" Nathan gave Akeno a surprisingly pleasant and genuine looking smile, only to instantly lose it in favour of a stern look "unfortunately you're also a moron…_how_ do you jump from wanting to break your friend out of an arranged marriage to flashing a guy you barely met last week?" Nathan asked with a bewildered voice causing the queen to frown slightly.

"You're a member of one of the most powerful families in existence, if anyone could help Rias right now it's you… can't you pull _any_ strings at all?!" the thunder priestess asked in desperation, the teen in front of her was the only reason that Rias's chances of getting out of the engagement were slim to none rather than just none at all.

Hearing Akeno's response, Nathan scoffed "Well…yes I can but that's not the point! You could've asked me normally first and then resorted to stripping if I refused. Not to say you shouldn't do that again, you've probably covered my masturbation material for the next two months. " the insomniac declared.

"Will you help or not?" Akeno asked impatiently, ignoring the insomniac's rant in order to cut to the chase.

"I'll do it on two conditions…" Akeno looked up at Nathan with hope in her eyes, whatever those conditions were she'd do her best to meet them. After all, her best friend's freedom and even her own freedom by extension as Rias's servant were both at stake. "Does Rias know that you've asked for my help?" Nathan asked.

"No…I'm doing this behind her back." Akeno felt a little guilty admitting this, but she was doing this in Rias's best interest.

"Good, you can't let her know that I've agreed to help if you want my plan to work." Akeno was a little perplexed by the first condition issued by the teen but she nonetheless let him continue without interruption. "If I remember correctly, Rias's older brother is the current Lucifer, which means he's in charge of the underworld's domestic affairs. My second condition is for you to set up a meeting between him and me after I get Rias out of her engagement. Rias and her entire peerage have to be at that meeting too… those are my conditions."

Akeno was both relieved and confused to hear Nathan's conditions, relieved because they were so simple but confused as to why Nathan wanted to meet Rias's older brother. Nevertheless, it was safe to assume that the two now had a deal.

"No problem, but can I ask why you want to see lord Sirzechs?" the Himejima let her curiosity get the better of her. Even though Sirzechs Lucifer was a very busy man he'd be unlikely to say no to an urgent request from any member of his little sister's peerage.

"You can ask… but I won't tell you." Nathan quipped as he rose from his seat and turned to leave the room, having concluded their agreement. Akeno also stood up and escorted Nathan to the door as customary of any self-respecting host. As Nathan walked out through the now open doorway, the thunder priestess called out to him.

"By the way, when you saw me in the shower room, you didn't look at me the way most men would have. If you carry on like that you might end up capturing my heart…" Akeno joked, returning to her teasing antics.

"Cool… I wonder how much I'll get for it on the black market..." Nathan casually replied as he descended the stairs, leaving a giggling Akeno to close the door behind him.

**To Be Continued…**

* * *

**The first girl in Nathan's harem will be Kuroka, but the game isn't over! You can still get the full list if you successfully guess the TV character that Nathan is based on. See you all next chapter…**


	3. Chapter 3

**Insomnia DxD**

**Author's note-**

**I'm sorry that this chapter took so much longer to make, I was abroad for a few weeks. I tried to type this chapter up on my phone but I just couldn't adjust to the mechanics of typing so much on a mobile device. That being said, I'm back and ready to continue the story from where we left off…**

**Disclaimer: I do not own Highschool DxD**

**Chapter 3: Checkmate**

* * *

Friday night had finally come around and with her upcoming bet with Nathan closing in, Sona couldn't help but await Nathan's arrival with mild excitement. The Sitri heiress had hoped that she'd find it stimulating to get the chance to play her favorite pastime with someone who had so far shown himself to be no less than her intellectual equal.

The hour the two had agreed on had finally come and the Sitri heiress was expecting the grey haired teen to arrive in the guest lounge of her manor in Kuoh any second. It was where their chess game was to be played and by extension where Nathan's possible future as a pseudo student council member would be decided.

As the student council president had expected, the room was soon entered by one of the manor's housemaids in order to announce the arrival of Sona's guest. After dismissing the servant, Sona stood up from her seat to properly greet her incoming guest. Not long after that, Sona's nemesis within Kuoh academy made his appearance being escorted into the room by the same maid who had announced his arrival moments earlier. With a bow at the two teen's general direction, the maid promptly left the room before closing the door behind her. Now that they were alone, Nathan addressed Sona.

"The maid that brought me in called me 'Mr. Pest'…It's not the alias we agreed on." Nathan stated in a mockingly accusing tone as he walked towards Sona. He was of course referring to the alias under which the Sitri heiress had instructed the maid to welcome him by as to avoid his true name being recognised by one of Sona's servants. One of the conditions the Sitri heiress had to agree to in order to be allowed to study in the human world was that her servants were to be her parent's eyes and ears. If Sona's father found out that a member of the famed Weslock family would be his daughter's guest he would more than likely request to meet with him, or even worse…attempt to bargain for an arranged marriage between his daughter and Nathan, and both Sona and her nemesis were most certainly not going to have that. Even so…Pest… Seriously? Nathan though, awaiting Sona's response.

"I saw that it fit your personality better, so I took the liberty of changing it." Sona replied with a smirk.

"So you make aliases based on the person's personality? No wonder you included the S-word in yours…Sona _Shit-_ori." Nathan retorted with a lesser smirk of his own as he approached Sona. Taking a closer look, the young man could see Sona was wearing a sky blue chiffon evening dress cutting just over her chest and reaching just under her knees. It was evident that Sona had put effort into her appearance befitting that of a high class devil heiress. Meanwhile Nathan, as per his usual manner of nonchalance regarding his appearance wore a light grey blazer over a black t-shirt that wasn't ironed and denim jeans.

Nathan and Sona both took a seat across from one another. In between them was a completely set chess board on top of an oak table supported by a thin wooden vine going into a spiral as if it had grown through the floor. The room itself looked very lavish and seemed to be decorated in some sort of forest theme with various plants and even a small wooden fountain at the centre of the room.

"Before we begin, I have a proposition." Sona stated, directing Nathan's attention from observing the room back to her.

"I'm flattered but wouldn't that defeat the purpose of me using an alias? I mean don't get me wrong, you are my type but the-"

"You know that's not what I meant…" Sona interrupted the grey haired teen's latest sarcastic remark, and to her credit she also resisted all urges to show her irritation, a considerable feat given who she was talking to. After the Sitri heiress recomposed herself, she once again addressed Nathan. "If you are going to be a de facto member of the student council, I'm going to need to know more about you. So, every time I capture one of your pieces that isn't the King, a Pawn, or the queen, I'll be allowed to ask you one question about yourself and vice versa." Hearing the Sitri heiress' offer, Nathan sat back against his seat in thought.

"And when I capture your pieces I can ask you _anything?"_ Nathan asked with a slight smile of mischief making the bespectacled woman doubt if her proposition really was a good idea.

"Anything _Appropriate…"_ Sona replied. Nathan sighed and shrugged his shoulders.

"That's no fun…but fine, I'll play along with your little kindergarten get-to-know-me activity. Can we get on with it now?" The grey haired teen relented and in response, Sona activated the chess clock facing the chess set and made the first move, assuming the side of the white pieces.

Early on in the game, the first valuable exchange happened with Sona sacrificing her white square bishop to capture one of Nathan's knights. Turning towards her opponent, Sona began with asking one of the questions she had thought of prior to their game.

"Why are you so fascinated with solving puzzles?" Sona asked, it was exactly how Nathan though Sona was going to phrase it… short, direct, and to the point. However, unfortunately for the Sitri heiress Nathan didn't plan on returning that sentiment in kind.

"It's all just practice in the hope that one day I'd be able to deduce the colour of your underwear. For today I'm guessing baby blue with white frills at the top?" Nathan sarcastically inquired and was secretly surprised to see Sona try to suppress a blush of embarrassment.

"I'm usually curious about how you get to your conclusions but this is one I'd rather not know." Sona stated, confirming that Nathan's random guess was in fact correct as she made a slight motion with her arms in the hopes of preventing Nathan from undressing her with his eyes. "I thought I said nothing inappropriate…" Sona complained.

"You said no inappropriate _questions_… you didn't say anything about inappropriate _answers_." Nathan retorted before glancing at the chessboard in front of him once again with his tired gaze. "Oh look…" Nathan said as he moved on of his pawns diagonally to capture the bishop that Sona had sacrificed. After placing the white bishop piece at the side of the table away from the board, Nathan pressed the button on his side of the chess clock. "My turn…"

After a few seconds of thinking of a question to ask, since the ones he had originally intended to ask were ruled out by Sona, Nathan finally stumbled onto something he was somewhat curious of.

"What brought you to Kuoh town?" Sona was admittedly a little taken aback by Nathan's question, more specifically because of the way he had asked it. Nathan's tone wasn't at all acerbic and Sona didn't sense a trace of sarcasm in his voice, it was evident that his question was fuelled by sincere curiosity rather than a half-hearted attempt to pass his turn. Seeing that, Sona decided to return his sincerity with her answer.

"It has been a lifelong dream of mine to establish a rating game school in the underworld. So far those kinds of institutions are only available to high class devils and other devil nobility. I want to create a school which is indiscriminate of the student's social status...But before I could establish a school, I needed to know how to run one, so I decided that I'd become the student council president of a human school so I could learn its system. And I didn't really choose Kuoh town, it just happened to be the only devil embassy that had an open position for devils to run it…" Sona glanced up at Nathan and sure enough, he was still listening to her story. Although she wasn't surprised at that fact, Sona was still inwardly glad that Nathan was returning the interest that the Sitri heiress had shown in him.

After a few more moves it had finally come to the point where Sona and Nathan would be exchanging valuable pieces again. This time however it was Nathan who initiated the trade by capturing Sona's remaining bishop with his knight, giving himself the privilege of asking the next question in exchange for leaving one of his own bishops exposed to Sona's queen.

"I know that almost all female high-class devils your age are already arranged to marry a suitor chosen by their parents to maintain their family's influence and whatnot… but judging by the fact that I have to use an alias here, and also the fact that you're not wearing an engagement ring I can tell you aren't one of them…how come?" Nathan asked, placing Sona's remaining bishop at the side of the table to join the first one before pressing the chess clock button on his end signalling that it was Sona's move.

"My parents did have a suitor arranged for me but I managed to break the engagement off. I challenged him to a chess game and won my freedom…I refuse to marry anyone who is intellectually inferior to me…" Sona proclaimed explicitly.

"Wow…you sure you wanna set the bar that low?" Nathan casually remarked as per his childish personality. In this case however, Sona decided to give him a run for his money.

"That's tough talk from someone who's about to lose his queen piece..." Sona replied with a triumphant smirk as she ignored the unprotected bishop that Nathan was offering for their current exchange in favour of positioning one of her knights so that it was putting Nathan's king in check while also forking his queen. In reaction to this, Nathan took another look at the chess board. His exhausted eyes bore into the wooden pieces as he analysed every possible move he could make…or at least he pretended to… he already knew he was going to win ever since Sona chose to ignore the bishop he had offered.

"I think that's game…" Nathan remarked as he moved his king out of harm's way leaving his queen vulnerable to Sona's knight.

"Giving up already? The Sitri heiress teased.

"I wasn't talking about me…" Nathan added, causing Sona to look at the grey haired teen in confusion. "My bishop wasn't the bait…the queen was. After you take my queen, I'll bring my rook out to put your king previously protected by your knight in check. Then, after you block with your own rook I'll bring the bishop that you chose not to capture forward to put your king in check again. From there your only option will be to block that with your queen and after you do that I'll take your rook with my own to force your king to move over to the square on his left where I'll pin him by capturing your queen with my remaining knight instead of the bishop that was threatening it previously. Even if you back out of taking my queen now it will be too late since either my queen or my bishop will still be free…check-mate." Nathan concluded leaving Sona completely dumbfounded by his revelation. After inspecting their piece's positions on the board over and over again thoroughly analysing and re-analysing all possible moves she could make, the Sitri heiress sighed in defeat.

"I'm impressed, I never expected you to utilize one of your key pieces as bait." Sona proclaimed. Seeing her nemesis's inevitable victory, the Sitri heiress decided to capture the bishop that was originally offered to her allowing the black queen piece she had previously trapped with her knight to escape. "There…" Sona said as she placed Nathan's captured bishop on the side of the table and pressing her end of the chess clock. "You owe me one more answer and then I'll resign the game." The Sitri heiress announced.

"Alright but make it quick, my porn isn't gonna watch itself…" Nathan nonchalantly accepted as he reached into his blazer pocked to retrieve two pills which he immediately brought up to his mouth and swallowed. Seeing this, Sona decided to act on her curiosity about this particular habit of Nathan's while ignoring his vulgar remark.

"Why do you take those pills… what are they? And please give me a real answer this time." Sona requested. Hearing this, Nathan sighed in exasperation and sat back into his chair. Realising that he'd probably have to satisfy the Sitri heiress' curiosity sooner or later, Nathan decided that it'd be best to get it out of the way now instead of having the student council president pester him about it all the time.

"The last time I slept was almost ten years ago... a couple of years into it, my medical _genius_ of a brother eventually managed to come up with this experimental drug…but after a while I noticed that all it really did was manage the pain from the insomnia a little and stop me from dying from the lack of sleep. It didn't make me feel any less tired and to top it all off, it turned my hair grey over time. But it was still better than nothing so my brother had me trained in medicine so that I could work in one of his clinics to repay him. But you already know those last two parts, the cat girl already told you…" Sona's eyes immediately widened at hearing the insomniac's confirmation of his past encounter with Koneko.

"So the boy who saved Rias's rook…?" At first the Sitri heiress was confused as to how Nathan knew that Koneko had mentioned the latter's past with him, but Sona figured that Nathan just put two and two together after noticing that the nekoshou left a little later than everyone else after Nathan's first encounter with the Gremory and Sitri groups at the student council room.

"Uh huh, Small world, I know… can we finish this now?" Nathan deadpanned, snapping Sona out of her awed state.

"Very well, I resign the game. Nathan Weslock…It is my privilege to welcome you as the newest member of the Kuoh academy student council." Sona reached over to a nearby drawer from which she took out a small piece of paper and handed it to Nathan. "This is your first assignment." Taking the paper from her, Nathan briefly scanned it over and gave the Sitri heiress a puzzled look.

"A party invitation?"

"Not just any party… it's an important annual gathering of all of the representatives of the elite schools both within and around the Kouh prefecture. Everyone from student council presidents to school administrators and benefactors are going to be in attendance. Every student council attending would need to show up with at least one male and one female representative, so you will be accompanying me and Tsubaki." Sona explained.

"Unless Saji has somehow found a way to grow a vagina during the last few days, you guys don't need me…" Nathan protested.

"Actually I was hoping that you'd come instead. I figured that you'd be accustomed to high profile gatherings due to your family's status. I'm not sure that Saji's quite ready for high society yet… I need someone with experience."

"Yeah I bet you do~" Nathan coyly remarked and smirked as he noticed a slight hue of red on Sona's face.

"You know, I can still blow your cover to my servants if I want to… and I will if you continue acting like a pervert." Sona reminded.

"Doing that would just increase the minimal chances of our families arranging a marriage between us. Instead of blowing my cover, are you sure you don't just wanna blow me instead?" The grey haired teen quipped, his teasing grin widening as Sona's face reddened.

"You're such a pig…"

* * *

For the high school students around the world Saturday is known as a day of relaxation, rest, and recovery from the stresses of the academic life…unless you're one of the suckers who somehow got themselves into an afterschool club or in Nathan's case…getting some devil princess out of an arranged marriage she doesn't want, so all in all a pretty bothersome experience all together.

On this particular Saturday, our favourite pill popping protagonist found himself sitting on top of the old Kuoh schoolhouse's clock tower, rotating his half empty bottle of pills in aimless boredom. Moments later, the ceiling hatch leading to the clock tower opened and out of it climbed Akeno Himejima, one of Kuoh academy's two great ladies and the second most popular girl on campus...not to mention the very woman who had given Nathan the "Au Naturel" a few days ago. Closing the hatch behind her, Akeno joined Nathan in sitting down in the clock tower for a conversation…a conversation without any nudity to Nathan's slight disappointment, but oh well.

"The cameras in the clubroom are installed as you asked, but what do you need them for?" the thunder priestess queried.

"I'm hosting an orgy there after you guys all leave to do your contracts, I'm planning to capture it in 4k for posterity…wanna join in?" Nathan replied, once again showcasing his sarcastic persona which elicited a giggle from Akeno.

"That wouldn't be very ladylike of me~" the thunder priestess answered, causing Nathan to give her a questioning look.

"Right… because a real lady waits at least one week before allowing a guy they barely know to see them naked…silly me." Nathan retorted, referring to Akeno's recent seduction attempt on the insomniac. In reaction to this, Akeno just rolled her eyes in exasperation before addressing Nathan with a teasing smirk on her face.

"It sounds like you regret not accepting my offer back then~" Akeno mentioned, catching the grey haired teen by surprise. After pondering about it, he replied.

"Maybe a little…" Nathan admitted, earning himself a doubtful look from Akeno "Okay, maybe more than just a little…" when Nathan saw that Akeno still wasn't letting up, he finally conceded. "Okay fine, choosing not to do you may have been the worst decision I've made in my entire life, happy?" Nathan admitted, causing the raven haired beauty to break into laughter.

Soon after that, Nathan sent Akeno back down to the occult research club room where she would be joining her fellow club mates in awaiting Riser's arrival. After hearing that Rias's fiancé would be visiting her in the human world, Nathan made Akeno request for the meeting to take place at the occult research club as per his plan to break up the engagement. For Nathan's plan to work, the meeting had to occur somewhere that he'd have an excuse to be, and what better place for that then the campus he went to school in? The most difficult part of Nathan's plan was keeping Rias in the dark about it but Akeno seemed to manage well in keeping her king uninformed.

Now it was just the waiting game…

* * *

Some fifteen minutes had passed since Akeno descended to the occult research clubroom and Nathan finally sensed the energy of an unknown teleportation circle materialize in the room below him, the time had finally come. As the teen stood up he reached inside his blazer pocked and fished out his bottle of pills, taking two of them out before placing the plastic bottle back into his pocket. As Nathan stood up to approach the hatch, he tossed the two pills in his hand upwards only to catch them in his mouth a second later.

As he was approaching the door to the occult research club, Nathan could hear an unfamiliar male voice coming from inside, to Nathan it was obvious who it was. As he reached his destination, Nathan proceeded to knock on the door and take in a deep breath, for now it was time for by far the most annoying and mentally torturous part of his plan…being polite. Being the narcissist Nathan was, he hated having to occasionally put on the act of being nice or polite, even if it was for his own benefit or gain. After all, Nathan was a proud man of principle, he didn't exactly believe he was above others per say, but he did hold on tightly to the belief that he shouldn't have to intentionally change his personality for anyone else, even for a little thing such as a temporary farce.

Akeno found herself feeling immense relief wash over her as she heard two knocks on the occult research club door. Rias was also on the same boat, hoping that whatever was behind that door would put even a moment's distance between her and the inevitable wedding with Riser. Without hesitation, the redhead answered the knock on the door by calling for whoever was knocking to come in. To the Gremory heiress's surprise…and minor disappointment, it was none other than her friend's nemesis who had entered the room.

Upon walking inside the room, Nathan had immediately noticed that the entire occult research club had been gathered by Rias's desk along with two unfamiliar faces, one standing in the middle of the room while the other sat on one of the Victorian styled couches. The one sitting down was a tall, handsome-looking man with blond hair and blue eyes. He wore a maroon blazer with matching slacks over a plain white dress shirt. Judging by the man's high-and-mighty posture along with the arrogant expression his face adopted the moment he laid eyes on Nathan, the latter had correctly assumed that man to be Riser Phenex.

The other person whom Nathan didn't recognise was a beautiful woman with a buxom figure appearing to be in her early twenties with silver eyes and long silver hair tied in long braids. The woman wore a French maid outfit with long sleeves and a white maid headband. By the way the unknown woman carried herself, Nathan could tell she was of high birth within the underworld's social hierarchy, and yet she didn't seem to share any of the holier-than-thou bravado that the blond man was subtly displaying. Her expression was largely indifferent in reaction to Nathan's entrance, leading Nathan to correctly guess that she was but an observer to the events occurring before her.

From the moment of Nathan's entrance there was a tense silence in the room, or at least there was until Riser decided to break it.

"One of yours, Rias?" Riser asked with a subtle snarling undertone. Rias would be lying if she said she wasn't at least a little tempted to namedrop Nathan's family in an attempt to intimidate Riser, but the fact was that she wouldn't feel right if she were to bring a bystander into her mess, it would go against the values that she was raised with as a Gremory. And so with a sigh, the redhead quickly dismissed her fiancé's question.

"No, he's just a student here…" upon hearing Rias's answer, Nathan found himself gaining at least a little respect for the Gremory heiress. Even though Nathan didn't expect any less, the fact was that it took guts for Rias not to pin the vulnerable position she was in onto him for a chance at an easy way out, and the grey haired teen acknowledged that. But seeing as how Nathan now had everyone's attention from his sudden unexplained appearance, it was finally his chance to execute what he referred to as "Operation Mr. nice guy". And so, with one final yet discreet look at the cameras installed by Akeno around the room, Nathan was finally assured that they'd be able to capture all that transpired between himself and Riser on video.

It was finally time for Nathan to break the silence, with that in mind the grey haired teen turned and approached Riser until he was right in front of him.

"I don't believe we've met before, my name is Nathan, pleased to make your acquaintance." Nathan politely introduced himself and brought his hand up for Riser to shake it. The members of the occult research club couldn't be more confused, as evidenced by the way they were all exchanging baffled expressions with one another, this even included Akeno who herself wasn't even aware of Nathan's plan, albeit to a lesser extent than the others. The way Nathan had introduced himself to the Gremory and Sitri groups a couple of weeks back had led them to the assumption that Nathan would be rather nonchalant regarding the way he spoke with high class devils, and yet here he was speaking formally with a humble tone lacking a single trace of sarcasm.

Riser just looked back at the grey haired teen and then to his outstretched hand. Without warning, the high class devil violently slapped Nathan's hand out of the way.

"I care not about who you are or what your name is, lowborn. We're in the middle of a discussion beyond anything a commoner like you could ever imagine in your pathetic insignificant life. Get out of my sight this instant!" Riser snarled as he looked down on the sleep deprived teen.

Well that was easy…Nathan had expected that he'd have to subtly yet politely annoy Riser into lashing out in front of the cameras. But the grey haired teen had gotten what he needed, and so it was time to make his exit.

"Well …I guess I'll take my leave then…" Nathan said with a strained smile as he walked back to the door he came from. As he put his hand on the door knob, Nathan turned to the occult research club and addressed Rias directly for what would be his first snarky remark since his entrance a minute ago...what could he say? He couldn't help himself. "Oh, by the way, Gremory… the student council president wanted to talk to you later... Something about her pitying you for getting engaged to a guy with a small package or some nonsense like that…poor guy whoever he is, he must be so insecure…" Nathan exclaimed in mock sympathy while pretending not to know who he was talking about. After that, the teen opened the door and exited the room. Issei for one, upon hearing Nathan's message to Rias, fell into hysterical laughter at Riser's expense while the other members of the occult research club had resorted to looking away as a means of avoiding the awkward atmosphere that Nathan's words had established.

In reaction to this, Riser's power flared up with rage as flames began encircling his fists, he was about to take off in Nathan's direction but was stopped in his tracks by the outstretched hand of the woman in the French maid outfit.

"I won't allow for things to escalate any further by order of Lord Sirzechs. If you refuse to accept those terms I will be forced to act. Please keep that in mind, Lord Riser…" The maid informed and put her hand back down after seeing that her message had gone through. Riser reluctantly dispersed the flames around his hands and sat back down on the couch in an attempt to reinstate his nonchalant, high-and-mighty image.

"Operation Mr. Nice Guy": Complete…ish

* * *

After what went down in the occult research club, Nathan decided to retire to a long relaxing session of solving an uneven, octahedron shaped Rubik's cube while lying down on a comfortable couch. It was going pretty well too until Nathan found himself getting smacked in the face with a paper fan by none other than the student council president herself. Tilting his chin up, Nathan caught the upside down view of Sona standing behind him folding her arms with the paper fan in hand.

"What? Am I not even worth rolling up a newspaper?" Nathan asked looking towards the Sitri heiress's improvised slapping fan. Instead of humouring the Insomniac's sarcastic query, Sona instead dismissed his question to ask one of her own.

"What are you doing in the Student council's office?"

Oh, right. Guess it did look kinda weird to all the student council members inside the room who watched on as Nathan casually entered their office just to lie down on one of their couches without saying a word. Could they blame him though? Those things were comfortable as hell… which is probably because they actually came from there.

"Didn't you say I was in the student council now?" Nathan asked.

"That doesn't mean you can just walk into the room like you own it, next time knock first" Sona reprimanded.

"Right… I forgot I could've accidentally caught you in the naughty act of redistributing the football club's spending budget, even _I_ wouldn't be able to handle a sight so erotic…" Nathan remarked with a sarcastic exaggerated expression of fear as he stood up from the couch.

"On another note, Tsubaki has an assignment with a client today and I want you to go with her." Sona requested…actually it sounded more akin to an order but to someone as stoic as her there was hardly a difference.

"Why do I have to go? I'm not in your peerage."

"True, but you aren't going to be doing official student council work either, you're going to have to pull your weight _somehow_." Sona finished. Leading Nathan to react the way she thought he would, by ignoring her request and turning to walk out of the door.

Well, Sona had prepared for this…

"Did I mention that our client is an underwear model?" Sona smirked as she saw the insomniac immediately stop in his tracks after hearing this. Without missing a beat, Nathan turned towards the student council vice-president.

"Lead the way, Shinra" Nathan said as he opened the door leading to the corridor outside of the student council room.

"We're teleporting there…" Tsubaki informed.

"Even better, we can aim for her bedroom…if we're lucky, we can catch her changing." Nathan remarked with a subtle hint of genuine enthusiasm.

"…"

* * *

When Nathan and Tsubaki teleported, they found themselves in a spacious living room with brand new genuine leather furniture, the entire floor seemed to be decorated with pictures of authentic modern art and the occasional sculpture here and there. After some further observation Nathan saw that they were standing in an exquisite penthouse-like suite. After Tsubaki announced her and Nathan's arrival the duo heard footsteps coming from around the corner leading to one of the corridors.

Soon after that, the figure of a young woman emerged from the corner. She was of petite build with a pretty face, yellow eyes and shoulder length amber hair complimented by her freckles. She looked to be of European heritage. Regarding the woman's attire, she wore a white cashmere blouse and light denim designer jeans along with cosy wool slippers. However to Nathan, the most distinctive feature to this woman was the small tattoo with minor reddening and scabs around it of the Virgo zodiac sign on her right wrist. This woman really did appear to be a model, Sona wasn't lying. When the woman noticed Tsubaki standing in the middle of the living room, she smiled at the female devil and introduced herself.

"You must be the devil from the house of Sitri I requested. My name is Monique Wilde, pleased to meet you." the woman said in a cheery voice as she sat down on one of her stylish leather futon's and crossed her legs. "Please, take a seat" Monique gestured to the matching leather couch in front of her. Tsubaki accepted the offer and sat down across from the young woman with Nathan following in tow.

"Good day Ms. Wilde, My name is Tsubaki…" Tsubaki introduced herself and then gestured to the grey haired insomniac before introducing him as well. "And this is Nathan, how may we be of help?" Upon noticing Nathan's presence in the room, Monique couldn't help but scowl subtly.

"I wasn't told that you'd be accompanied by a man…" Monique pointed out with a subtle hint of irritation. Both Tsubaki and Nathan were confused as to why this woman would have an issue with a man being present, but it wasn't long before Nathan figured it out. Upon a more analytical glance around the room they were in, Nathan saw an array of photos and posters depicting various feminist rallies and quotes written on the posters in noticeably bold fonts. So far it appeared that this woman didn't have much of an appreciation for men… which was interesting considering the fact that she was also wearing a wedding ring.

"My master insisted that he'd assist in carrying out our service, would that pose an issue?" Tsubaki asked with a little confusion in her voice.

"I was just hoping to have some girl talk is all, but I suppose if he _must_ stay, he can as long as he doesn't interrupt us…" Monique offered. Tsubaki looked questioningly at Nathan, who just shrugged in response. Tsubaki turned back to the amber haired woman and assured her that Nathan's presence wouldn't pose an issue with their conversation. And so the "girl talk" session began…

After solving his octahedron shaped Rubik's cube… for like the sixth time since he'd zoned out of the conversation between Tsubaki and Monique, Nathan looked at the clock on the wall and realised to his horror that the women had only been talking for just short of fifteen minutes. With pretty much nothing to do to keep himself entertained, the insomniac decided to just sit back and stealthily eavesdrop on the conversation.

"…Oh, and you wouldn't believe how disgusting some of the men I work with are, always leering at me at any chance they get, even when I'm not on the catwalk or when I show them that I'm married." Monique said as she gestured to her wedding ring. "Honestly, men can be such pigs sometimes…" Monique stated. To which Tsubaki only nodded nervously, unsure of what to say. Hearing Monique's words, Nathan rolled his eyes in rather obvious exasperation, which managed to catch Monique's attention. "Oh I'm sorry, something you wanted to say?" Monique asked with a biting undertone. Nathan opened his mouth to speak but saw that Tsubaki was giving him a threatening glare. Nathan decided against saying what he was going to say, but he knew it was a little too late to hold his tongue. And so, Nathan decided to cover up what he was originally going to say by asking for some water instead.

Proud over her small "victory" over the young man, Monique decided to take the passive aggressive approach of humouring Nathan's request.

"Jack, would you be a dear and get me some water?" Monique shouted in the direction of the room adjacent to the lounge they were in. After a few seconds passed, the trio heard footsteps coming towards them and shortly after that a male figure emerged from the same corner where Monique had made her entrance. The man looked to be in his late twenties or early thirties with black hair and a cleanly shaven face. He wore a purple cotton robe with matching slippers and carried a glass of water with a coaster under it which he placed on the small coffee table between the couch that Nathan and Tsubaki were sitting on and the futon that Monique sat on. This allowed Nathan to see that the man had the same matching Virgo zodiac tattoo as Monique but on his left wrist instead of his right. Both his and Monique's tattoos seemed to be made around the same time, but the man's wrist had completely healed unlike Monique's. Upon noticing this, Nathan suppressed a devious smile as he got an idea.

"This is my husband and hair stylist, Jack." Monique introduced.

So she wasn't a lesbian then, go figure…

"Jack, these two are the devil servants from the house of Sitri that I requested. Tsubaki and…" Monique started snapping her fingers pretending to try and remember Nathan's name.

Nathan decided on keeping quiet about not being a servant of the house of Sitri…or a devil for that matter, he figured that it would be more enjoyable if his nemesis within Kuoh Academy took responsibility for what he did next…

The insomniac turned to Monique's husband. "Oh my name isn't important, I'm just the guy who figured out your wife is cheating on you…" Nathan casually stated and easily kept a straight face under the looks of shock from the other three.

"W-what?" Jack uttered in confusion.

"You two have matching tattoo's which I assume you got at the same time, judging by how much the ink has set on each of your wrists. Yours has already healed but Mrs Two-timer over here still has the scabs and reddening from when the needle pierced her skin…" Nathan stated and then turned to the still flabbergasted Monique "This means that something is attacking your immune system, preventing it from healing your wrist…you have AIDS…" Nathan concluded, forcing a long awkward silence into the room which was only broken by the equally shocked husband.

"Is this true?" Jack asked, fearing the answer. Monique turned as to not look him in the eye.

"It was during the time we had that fight…I was pissed at you and drunk at a bar…I didn't wanna call you to come and take me home…so I called my agent… Jack I'm sorry…it was only meant to be a one night stand, but we just kept seeing each other and…" Monique stopped and broke into tears moments later, which turned into sobs as she saw her husband angrily storm out of the room. With despair in her eyes, Monique turned to Nathan.

"Am I going to live…is this thing gonna kill me?" Monique asked in desperation. With both her and Tsubaki looking at him for an answer, the former fearing for the worst and the latter simply out of curiosity, Nathan sighed.

"Relax, you don't have AIDS…it's just an allergic reaction to the ink they used…" Nathan revealed leaving the two women stunned.

…

"YOU BASTARD… YOU LIED TO ME!" Monique yelled through her tears.

"Yup, just like you've been doing to your husband… Except I did a better job…" Nathan stood up and walked to the middle of the room, with Tsubaki awkwardly following in tow. "Men really are pigs aren't they?" Nathan said with a sarcastic, satisfied smile.

Back at the student council's office, a white magic circle appeared in the middle of the room from which a smug Nathan and an exasperated Tsubaki emerged from.

"How did it go?" Sona asked…unsure of whether or not she wanted to know the answer.

"We're getting sued…" Tsubaki revealed as she walked to take her place at her master's side. Upon hearing this, everyone in the room shot questioning looks at Nathan until Saji voiced everyone's question.

"What the hell! You two were gone for less than 20 minutes!" In response to this, Nathan walked towards the door leading to the corridor outside before opening it and turning back to the student council members.

"I'm _that _good…" the insomniac stated before tossing his Rubik's octahedron into Sona's hands and exiting the room, leaving the other student council members except for Tsubaki to exchange looks of confusion between one another.

* * *

Three days after his visit to the human world, Riser was in his room getting dressed in preparation for an upcoming meeting that he had to attend along with his family. The way the event had been briefed to him let on that it was a meeting of high importance. The gist was something about the family finally being able to meet with an important business partner face to face. Riser's father, the head of the Phenex clan himself had been sceptical about accepting investments from and trading with an anonymous entity, but in the end the reason why the Phenex family had accepted doing business with someone hiding their identity was simple.

While the person behind it all remained anonymous themselves, they didn't try to hide the vast amount of stocks and shares it owned throughout both the human world and underworld. After multiple investments allowing some of the Phenex family's newest business projects to become major successes, a certain level of trust was established between the Phenex family and the person on the other side. Trust that eventually lead to the anonymous person behind all those shares offering Lord Phenex the chance gain a 50/50 share on one of the unknown business partner's largest businesses in the human world worth over 4 billion dollars of human world money. An offer like that not only allowed the Phenex family to gain another secure source to further their already massive income, but also the opportunity to further expand their influence into the human world…something that their associates of the house of Gremory had them completely beat in.

So all in all, that business deal was pretty important, so important that the unknown person behind all those stocks and shares had finally agreed to a personal invite to meet the members of the Phenex clan face to face in their place of ruling… the renowned Phenex palace in the underworld. It was the very meeting that the Phenex clan's third son had been preparing for.

As Riser finished fastening his favourite pair of gold and diamond encrusted cufflinks, he felt the familiar sensation of his maroon blazer being wrapped around his shoulders. After threading his arms through the sleeves, he turned around to face his assistant and queen.

"That would be all, Yubelluna." Riser addressed his queen. She was a beautiful, buxom woman with long purple hair covering her right eye and reaching down to her waist, her eyes being the same colour as the hair that concealed one of them. She wore a dress consisting of an elaborate navy blue tunic top with gold accents revealing much of her cleavage and a pale blue long skirt which cut to display her thighs. She wore black shoes over matching stockings held by garter belts. In response to being dismissed by her master, she bowed to him before exiting the room.

Truth be told, Riser wasn't even supposed to be at the meeting. His father had originally only requested for his first and second born sons to be present at the meeting. However, the Phenex family's second son had been unable to attend the gathering due to being busy running a substantial portion of the underworld's media. As a result, Lord Phenex had requested for Riser to attend in his older brother's stead, something that Riser wasn't too ecstatic about, but in the end even he had to obey his father's wishes.

Upon arriving at the grand conference hall where he and his family were to await the arrival of their mysterious business partner, Riser nodded in greeting to his father before taking a seat at the large conference table alongside his older brother, Ruval, the eldest child of the Phenex family and heir to the clan, and Ravel, their younger sister and the youngest child and only daughter of the family.

Ruval had the appearance of a handsome-looking man in his mid-twenties with short blonde hair and blue eyes. He wore a dark blue business suit over a white dress shirt complete with a black necktie. Meanwhile his younger sister Ravel had the appearance of a beautiful girl with eyes and hair the same colour as her brothers' with her hair being styled in twintails with large drill-like curls with blue ribbons keeping them in place, allowing a few bangs to hang over the bridge of her nose and forehead. Her attire consisted of a light purple dress with dark accents and a bow at the front of her chest that matched the colour of the ones that tied her twintails together.

Soon enough, a knock was heard at the main entrance to the hall, once Lord Phenex called for the person to enter the door opened to reveal a woman with brown hair wearing a maid costume. Before anything else, the woman bowed in respect and announced her message.

"Lord Phenex, your guest has arrived." At the message, every Phenex family member perked up in curiosity.

"Excellent, please show him in." The head of the house of Phenex requested leading the maid to bow once again and leave the room only to return shortly after.

"Right this way…" the maid called out to someone still behind the door. Moments later, the person emerged.

Short, dark, grey hair, sleepless yet focused icy blue eyes, and those distinct shadows under them that bared all there was to see about their owner's lack of sleep. As Nathan walked into the grand conference hall, he noticed the eyes of the Phenex family all looking him up and down with curiosity and a little surprise. Nathan wore a white dress shirt under a loose fit grey blazer with matching slacks, all of which had been neatly ironed, going a little against Nathan's character. Thank God Sona wasn't there to see him like this… the insomniac could only imagine how much of a nuisance it would be if the Sitri heiress were to raise her expectations for his appearance.

Pushing his nemesis within Kuoh academy out of his mind, Nathan focused on his whereabouts, allowing his eyes to wonder around the grandiose hall he was invited into. The area was full of elaborate decorations and works of art ranging from original paintings and statues to exquisite furniture forged with the finest craftsmanship money could secure. The most notable decorations around the areas of the palace that Nathan had seen were the numerous emblems of the Phenex family situated everywhere the eye could turn to in the Phenex castle.

The members of the house of Phenex welcomed Nathan with smiling faces, except for one… after recognising the grey haired teen as the person he rudely dismissed back at the occult research club three days ago, Riser felt the feeling of dread wash over him as he made eye contact with the guest.

"As the head of the house of Phenex, it is a pleasure to welcome one of our most treasured business partners to our palace, please, Join us at the table." The head of the Phenex family invited and gestured to the central chair at the opposite side of the spacious conference table where the Phenex family members were sat at. Nathan noted that in contrast to his third son, Lord Phenex sounded incredibly polite and humble. The Phenex family in general were known throughout the underworld to be very humble people, oddly enough Riser just happened to be the exception that proved the rule. Accepting Lord Phenex's offer, Nathan took the central seat to be situated just across from the head of the Phenex clan himself.

"My family and I have waited for an opportunity to meet you in person for quite some time now. I believe some introductions are in order. My name is Reanor Phenex, current head of the house of Phenex." The now named Reanor stated. He looked to be a man in his late twenties with shoulder length blond hair that spiked at the back. He wore noble clothing consisting of a dark red blazer with various brooches and other jewellery pined to its lapel under a thin white fur coat only suitable for someone within the top ranks of devil nobility. After his introduction, Nathan turned to face the woman sat beside the Phenex family head.

"My name is Eleanoria, Lady to the house of Phenex." Eleanoria was a beautiful woman with a similar appearance to her daughter, albeit in her early twenties and with her hair done up very high with ornate decorations. The Phenex matriarch then looked to her children. "This is our daughter, Ravel." In response to being mentioned by her mother, the young girl stood up from her chair and bowed while lifting her dress slightly in greeting courtesy. Lady Phenex then turned to her sons. "This is Ruval, our eldest son, and this is-".

"Lord Riser and I are already acquainted." Nathan politely cut the Matriarch of the Phenex family off as he looked at her youngest son with a subtle passive aggressive smile. Riser felt cool sweat run down the back of his neck as he remembered the time he had first met Nathan back at the occult research club. The third son of the Phenex family could never have imagined that the "commoner" that had stood in front of him three days ago would turn out to be one of his fathers most significant business partners. "Please forgive me for keeping my identity a secret for so long and not introducing myself earlier, my name is Nathan Weslock…"

For an awkward yet brief period of time, no one present at the meeting said a word. The members of the Phenex family exchanged the occasional look of intense surprise with one another, as if they were telepathically questioning if they had misheard the grey haired teen in his introduction. But who could blame them? The Weslock family was widely known yet very rarely discussed throughout the nobility of the underworld, it was a known fact that there wasn't a devil family in existence that even came close to rivalling the amount of wealth that the Weslocks had. Many among the devil faction also speculated that the Weslock family could even buy the entire underworld if they wished, the amount of wealth they had was completely incalculable by the underworld's standards.

"Surely you jest, the Weslock family doesn't usually take interest in the underworld's affairs." Lord Phenex asked, being the first member of the Phenex family to compose themselves enough to break the silence.

"Well, I guess you can just think of this meeting as the exception that proves the rule then." Nathan quipped, revealing some of his nonchalance in the process. However, the grey haired teen knew that he was there with a purpose, and so he couldn't afford to be snarky… at least not in front of Riser's entire family if he wanted his plan to work. "Before we get down to business, I would like to speak with Lord Riser…in private." Nathan requested, making the aforementioned son and his father exchange a look of curiosity.

* * *

"Whatever it is you want from me, make it quick." Riser demanded with the same arrogant tone he had used in his first encounter with Nathan since they were now in the corridor leading to the conference room and therefore out of earshot from the rest of the Phenex family.

"You're going to cancel your engagement to Rias Gremory." Nathan stated in a careless tone. Hearing this made the devil from the house of Phenex chuckle at the grey haired teen's absolution.

"And why am I going to do that?" challenged Riser in a smug tone, allowing his arrogant smirk to form yet again. In response to this, Nathan summoned a palm sized magic circle and held his hand out. Soon enough, from the magic circle emerged a holographic image depicting the occult research clubroom along with its members. At first it looked like a still image, but then Riser noticed a Phenex teleportation circle manifest itself within the image while the holograms of the occult research club members reacted to it. The third son of the Phenex family quickly realised to his horror that what he was watching was footage from his encounter with Nathan from three days ago.

After Nathan was sure that Riser had seen enough to get the message, he dispersed the magic circle and turned to the blond man while sporting a confident smirk on his face.

"That's why." Nathan replied to Riser's daring query. In response to this, the Phenex family's third son let out a growl of frustration and angrily snapped his left finger. No more than a second later, Nathan found himself surrounded by fourteen women all wearing various revealing outfits. It didn't take long for the insomniac to figure out that he was surrounded by Riser's peerage. Looking around and observing the women that surrounded him, Nathan raised a questioning eyebrow at the man in front of him.

"Take your pick, you can take any one of them to do with as you please, but I need to have Rias." Riser offered, but Nathan picked up on the slight hint of desperation in the Phenex's voice. Just before Nathan was going to inform Riser that he was in fact not interested in taking the Gremory heiress for himself, two of the girls from Riser's peerage caught his eye. They were twin girls with bright turquoise hair and blue eyes, they each wore a school girl's gym class outfit and looked to be no older than twelve. Nathan gave Riser an accusing look upon seeing them within the ranks of the latter's harem.

"Those little girls are in your harem? Seriously? Well…I guess if their age is on the clock…" Nathan quipped sarcastically, causing a tick mark to form on Riser's forehead.

"You dare insult me? You're just envious that I have a plethora of women all to myself who are willing to act like porn stars for me all according to my whims!" Riser countered raising his voice while at the same time making sure not to be overheard by his family.

"You mean they fake their orgasms and you pay them?" Nathan retorted, earning himself a look of rage from Riser. Deciding that it was time to declare his final ultimatum, the insomniac once again addressed Riser. "Look… I don't give a rat's ass about Rias Gremory, but due to certain circumstances I can't let you marry her. So, you can either cancel the engagement voluntarily to keep our encounter from three days ago our little secret, or I can go back into that conference room, show your family the footage and refuse the business deal until they force you to cancel the engagement, leaving you single _and _on bad terms with your family… So what's it gonna be?"

* * *

Sat at her desk back at the occult research club room, Rias was reading a book on various rating game strategies that she could use in the future. After the occult research club had witnessed the encounter between Nathan and Riser three days ago, the Gremory heiress had been given the chance to fight for her freedom in a rating game match against her fiancé and his peerage. With only ten days given to train her peerage her chances looked as grim as they did before she was even given the option to fight, but she knew she had to make the most of it, hence why she had been studying those strategies so enthusiastically.

The Gremory heiress was a little startled by the sudden noise of the telephone on corner of her desk ringing. Deciding to give herself a small break, the Gremory heiress answered the phone.

From outside the old school building, Nathan watched though the window to the occult research clubroom as Rias's lips gradually formed into a small smile that progressively widened as the news of her freedom from her loathsome engagement to Riser were announced to her over the phone until she finally lost it and jumped out of her seat in ecstatic celebration. Soon enough, her loyal queen and best friend wondered into the room curious about what all the commotion was about only to find herself in a crushing bear hug of joy at the hands of her master. Once Akeno had been told the great news, she too rejoiced at her master's lifted burden and returned the hug.

Soon enough, the entire peerage was called back early from their contracts and celebrations quickly ensued over the cancellation of their master's unwanted arranged marriage, ending with Issei receiving a passionate yet meaningful kiss from Rias, who had decided that with her engagement out of the way it was finally time to lay the groundwork for a real relationship with the person she really loved.

"So, how did you do it?" Nathan turned around towards the source of the familiar voice and quickly realised that it was Sona, who stopped walking once she was next to him. Knowing that the entire story would be too bothersome to recount, Nathan decided to spare the Sitri heiress all the details and opted for a much shorter answer instead.

"I was nice…" Nathan summarized before turning around and heading to the exit at the school gates. Sona, who found herself slightly amused by his short answer, called out to the insomniac.

"I'm sure you were…" She said with a sarcastic grin "I'm going to retire for the night, and remember that I expect to see you at that gathering." With that, the Sitri heiress conjured up a white magic circle under her feet. Turning around, the grey haired teen called back out to her.

"By the way, you should expect to hear an angry message from Riser Phenex…something about you making fun of his small pecker…well then, goodnight." Sona's smirk instantly turned into an angry scowl upon hearing this and so the Sitri heiress quickly made a point to walk towards the insomniac to give him a piece of her mind. Unfortunately, she had forgotten that she had already activated her magic circle in the process, which led to a rather humiliating exit on her part resulting in her nemesis being the one to get the last word in.

**To be continued…**

* * *

**Damn, this chapter sure took a while, I do apologise for that. This is the last chance to get the full list of Nathan's harem as I will be revealing the character he is based on in the next chapter. But as for now, one of the other girls in Nathan's harem will be Akeno. **

**Till next time…**


End file.
